Octet / Reactions

Acetoacetic Ester Synthesis

Included in Reactions.

Substitution

Source Details

Id

acetoacetic-ester-synthesis

Name
{
  "en": "Acetoacetic Ester Synthesis",
  "ar": "Acetoacetic إستر تحضير",
  "cs": "Acetoacetic Ester Synteza",
  "da": "Acetoacetic Ester Syntese",
  "de": "Acetoacetic Ester Synthese",
  "el": "Acetoacetic Εστέρας Σύνθεση",
  "es-419": "Síntesis acétoacétique",
  "es-ES": "Síntesis acétoacétique",
  "es": "Síntesis acétoacétique",
  "fi": "Acetoacetic Esteri Synteesi",
  "fr": "Synthèse acétoacétique",
  "he": "Acetoacetic אסטר סינתזה",
  "hr": "Acetoacetic Ester Sinteza",
  "hu": "Acetoacetic Észter Szbantézis",
  "id": "Sintesis Ester Asetoasetat",
  "it": "Sintesi acétoacétique",
  "ja": "アセト酢酸エステル合成",
  "ko": "아세토아세트산 에스터 합성",
  "lv": "Acetoacetic Esteris Sinteze",
  "nb": "Acetoacetic Ester Syntese",
  "nl": "Acetoacetic Ester Synthese",
  "pl": "Acetoacetic Ester Synteza",
  "pt-BR": "Síntese acétoacétique",
  "pt-PT": "Síntese acétoacétique",
  "ro": "Sinteză acétoacétique",
  "ru": "Acetoacetic Эфир Синтез",
  "sk": "Acetoacetic Ester Synteza",
  "sl": "Acetoacetic Ester Sinteza",
  "sv": "Acetoacetic Ester Syntes",
  "th": "การสังเคราะห์เอสเทอร์อะซีโตอะซิติก",
  "tr": "Acetoacetic Ester Sentez",
  "uk": "Acetoacetic Естер Синтез",
  "vi": "Tổng hợp acetoacetic ester",
  "zh-Hans": "乙酰乙酸酯合成",
  "zh": "乙酰乙酸酯合成"
}
Type
{
  "en": "Substitution",
  "ar": "استبدال",
  "cs": "Substituce",
  "da": "Substitution",
  "de": "Substitution",
  "el": "Υποκατάσταση",
  "es-419": "Sustitución",
  "es-ES": "Sustitución",
  "es": "Sustitución",
  "fi": "Substituutio",
  "fr": "Substitution",
  "he": "התמרה",
  "hr": "Supstitucija",
  "hu": "Szubsztitúció",
  "id": "Substitusi",
  "it": "Sostituzione",
  "ja": "置換",
  "ko": "치환",
  "lv": "Aizvietošana",
  "nb": "Substitusjon",
  "nl": "Substitutie",
  "pl": "Substytucja",
  "pt-BR": "Substituição",
  "pt-PT": "Substituição",
  "ro": "Substituție",
  "ru": "Замещение",
  "sk": "Substitúcia",
  "sl": "Substitucija",
  "sv": "Substitution",
  "th": "การแทนที่",
  "tr": "Yer değiştirme",
  "uk": "Заміщення",
  "vi": "Thế",
  "zh-Hans": "取代",
  "zh": "取代"
}
Starting Material

CCOC(=O)CC(=O)C

Product

CCC(=O)C

Reagents

NaOEt, R-X, then H₃O⁺/heat

Mechanism
[
  {
    "smiles": "CCOC(=O)CC(=O)C",
    "description": {
      "en": "Ethyl acetoacetate: acidic α-H (pKa ~11)",
      "ar": "إيثيل acetoacetate: حمضي α-H (pKa ~11)",
      "cs": "Ethyl acetoacetate: kysele α-H (pKa ~11)",
      "da": "Ethylacetoacetat: acidic α-H (pKa ~11)",
      "de": "Ethylacetoacetat: acidic α-H (pKa ~11)",
      "el": "Ethyl acetoacetσεe: οξύic α-H (pKa ~11)",
      "es-419": "Etil acetoacetate: acidic α-H (pKa ~11)",
      "es-ES": "Etil acetoacetate: acidic α-H (pKa ~11)",
      "es": "Etil acetoacetate: acidic α-H (pKa ~11)",
      "fi": "Etyyliasetoasetaatti: acidic α-H (pKa ~11)",
      "fr": "Éthyle acetoacetate: acidic α-H (pKa ~11)",
      "he": "אתיל acetoacetate: חומצי α-H (pKa ~11)",
      "hr": "Ethyl acetoacetate: kiseo α-H (pKa ~11)",
      "hu": "Ethyl acetoacetnále: savic α-H (pKa ~11)",
      "id": "Etil asetoasetat: α-H asam (pKa ~11)",
      "it": "Etile acetoacetate: acidic α-H (pKa ~11)",
      "ja": "アセト酢酸エチル: 酸性α-H(pKa ~11)",
      "ko": "에틸 아세토아세테이트: 산성 α-H(pKa ~11)",
      "lv": "Ethyl acetoacetate: skabs α-H (pKa ~11)",
      "nb": "Etylacetoacetat: acidic α-H (pKa ~11)",
      "nl": "Ethylacetoacetaat: acidic α-H (pKa ~11)",
      "pl": "Ethyl acetoacetate: kwasowy α-H (pKa ~11)",
      "pt-BR": "Etil acetoacetate: acidic α-H (pKa ~11)",
      "pt-PT": "Etil acetoacetate: acidic α-H (pKa ~11)",
      "ro": "Etil acetoacetate: acidic α-H (pKa ~11)",
      "ru": "Ethyl acetoacetate: кислый α-H (pKa ~11)",
      "sk": "Ethyl acetoacetate: kysly α-H (pKa ~11)",
      "sl": "Ethyl acetoacetate: kisel α-H (pKa ~11)",
      "sv": "Etylacetoacetat: acidic α-H (pKa ~11)",
      "th": "เอทิลอะซีโตอะซิเตต: α-H เป็นกรด (pKa ~11)",
      "tr": "Ethyl acetoacetdee: olarakitic α-H (pKa ~11)",
      "uk": "Ethyl acetoacetate: кислий α-H (pKa ~11)",
      "vi": "Ethyl acetoacetate: α-H có tính axit (pKa ~11)",
      "zh-Hans": "乙酰乙酸乙酯:酸性 α-H(pKa ~11)",
      "zh": "乙酰乙酸乙酯:酸性 α-H(pKa ~11)"
    }
  },
  {
    "smiles": "CCOC(=O)CC(=O)C",
    "description": {
      "en": "Enolate alkylation",
      "ar": "Enolate ألكلة",
      "cs": "Enolat alkylace",
      "da": "Enolat alkylation",
      "de": "Enolat alkylation",
      "el": "Ενολικό ανιόν alkylσεiσε",
      "es-419": "Alquilación de enolato",
      "es-ES": "Alquilación de enolato",
      "es": "Alquilación de enolato",
      "fi": "Enolaatti alkylation",
      "fr": "Alkylation de l’énolate",
      "he": "Enolate אלקילציה",
      "hr": "Enolat alkilacija",
      "hu": "Enbancslát alkylnálion",
      "id": "Alkilasi enolat",
      "it": "Alchilazione dell’enolato",
      "ja": "エノラートのアルキル化",
      "ko": "에놀레이트 알킬화",
      "lv": "Enolats alkilesana",
      "nb": "Enolat alkylation",
      "nl": "Enolaat alkylation",
      "pl": "Enolan alkilacja",
      "pt-BR": "Alquilação de enolato",
      "pt-PT": "Alquilação de enolato",
      "ro": "Alchilarea enolatului",
      "ru": "Енолят алкилирование",
      "sk": "Enolat alkylacia",
      "sl": "Enolat alkilacija",
      "sv": "Enolat alkylation",
      "th": "การแอลคิเลตของอีโนเลต",
      "tr": "Eyoklde alkyldeiüzerinde",
      "uk": "Енолят алкілування",
      "vi": "Alkyl hóa enolate",
      "zh-Hans": "烯醇盐烷基化",
      "zh": "烯醇盐烷基化"
    }
  },
  {
    "smiles": "CCC(=O)C",
    "description": {
      "en": "Hydrolysis and decarboxylation → substituted ketone",
      "ar": "تحلل مائي و decarboxylation → مستبدل كيتون",
      "cs": "Hydrolyza a decarboxylation → substituovany keton",
      "da": "Hydrolyse og decarboxylation → substitueret keton",
      "de": "Hydrolyse und decarboxylation → substituiert Keton",
      "el": "Υδρόλυση και decarboxylσεiσε → υποκατεστημένο κετόνη",
      "es-419": "Hidrólisis y decarboxylation → substituted cetona",
      "es-ES": "Hidrólisis y decarboxylation → substituted cetona",
      "es": "Hidrólisis y decarboxylation → substituted cetona",
      "fi": "Hydrolyysi ja decarboxylation → substituoitu ketoni",
      "fr": "Hydrolyse et decarboxylation → substitut...
Tips
[
  {
    "en": "Makes substituted ketones (methyl ketones)",
    "ar": "يصنع مستبدل كيتونات (ميثيل كيتونات)",
    "cs": "Cini substituovany ketony (methyl ketony)",
    "da": "Makes substitueret ketones (methyl ketones)",
    "de": "Makes substituiert ketones (methyl ketones)",
    "el": "Makes υποκατεστημένο κετόνες (methyl κετόνες)",
    "es-419": "Makes substituted cetonas (metil cetonas)",
    "es-ES": "Makes substituted cetonas (metil cetonas)",
    "es": "Makes substituted cetonas (metil cetonas)",
    "fi": "Makes substituoitu ketones (methyl ketones)",
    "fr": "Makes substituted cétones (méthyle cétones)",
    "he": "יוצר מותמר קטונים (מתיל קטונים)",
    "hr": "Cini supstituiran ketoni (metil ketoni)",
    "hu": "Makes szubsztituált ketonbancsk (methyl ketonbancsk)",
    "id": "Membuat keton tersubstitusi (metil keton)",
    "it": "Makes substituted chetoni (metile chetoni)",
    "ja": "置換ケトン(メチルケトン)を作る",
    "ko": "치환 케톤(메틸 케톤)을 만듦",
    "lv": "Padara aizvietots ketoni (metil ketoni)",
    "nb": "Makes substituert ketones (methyl ketones)",
    "nl": "Makes gesubstitueerd ketones (methyl ketones)",
    "pl": "Czyni podstawiony ketony (metyl ketony)",
    "pt-BR": "Makes substituted cetonas (metil cetonas)",
    "pt-PT": "Makes substituted cetonas (metil cetonas)",
    "ro": "Makes substituted cetone (metil cetone)",
    "ru": "Делает замещенный кетоны (метил кетоны)",
    "sk": "Robi substituovany ketony (metyl ketony)",
    "sl": "Naredi substituiran ketoni (metil ketoni)",
    "sv": "Makes substituerad ketones (methyl ketones)",
    "th": "สร้างคีโตนที่ถูกแทนที่ (เมทิลคีโตน)",
    "tr": "Makes sübstitüe ketüzerindelar (methyl ketüzerindelar)",
    "uk": "Робить заміщений кетони (метил кетони)",
    "vi": "Tạo xeton đã thế (methyl xeton)",
    "zh-Hans": "制备取代酮(甲基酮)",
    "zh": "制备取代酮(甲基酮)"
  },
  {
    "en": "Decarboxylation of β-keto acid",
    "ar": "Decarboxylation من β-كيتو حمض",
    "cs": "Decarboxylation z β-keto kyselina",
    "da": "Decarboxylation of β-keto syre",
    "de": "Decarboxylation of β-keto Säure",
    "el": "Decarboxylσεiσε της β-keto οξύ",
    "es-419": "Decarboxylation of β-keto ácido",
    "es-ES": "Decarboxylation of β-keto ácido",
    "es": "Decarboxylation of β-keto ácido",
    "fi": "Decarboxylation of β-keto happo",
    "fr": "Decarboxylation of β-keto acide",
    "he": "Decarboxylation של β-קטו חומצה",
    "hr": "Decarboxylation od β-keto kiselina",
    "hu": "Decarboxylnálion of β-keto sav",
    "id": "Dekarboksilasi asam β-keto",
    "it": "Decarboxylation of β-keto acido",
    "ja": "β-ケト酸の脱炭酸",
    "ko": "β-케토산의 탈카복실화",
    "lv": "Decarboxylation nav β-keto skabe",
    "nb": "Decarboxylation of β-keto syre",
    "nl": "Decarboxylation of β-keto zuur",
    "pl": "Decarboxylation z β-keto kwas",
    "pt-BR": "Decarboxylation of β-keto ácido",
    "pt-PT": "Decarboxylation of β-keto ácido",
    "ro": "Decarboxilarea β-cetoacidului",
    "ru": "Decarboxylation из β-keto кислота",
    "sk": "Decarboxylation z β-keto kyselina",
    "sl": "Decarboxylation od β-keto kislina",
    "sv": "Decarboxylation of β-keto syra",
    "th": "ดีคาร์บอกซิเลชันของกรด β-คีโต",
    "tr": "Decarboxyldeiüzerinde β-keto olarakit",
    "uk": "Decarboxylation з β-keto кислота",
    "vi": "Khử carboxyl của axit β-keto",
    "zh-Hans": "β-酮酸脱羧",
    "zh": "β-酮酸脱羧"
  },
  {
    "en": "Can alkylate twice",
    "ar": "يمكن alkylate twice",
    "cs": "Může alkylovat dvakrát",
    "da": "Kan alkyleres to gange",
    "de": "Kann zweimal alkyliert werden",
    "el": "Can alkylσεe twice",
    "es-419": "Puede alquilar dos veces",
    "es-ES": "Puede alquilar dos veces",
    "es": "Puede alquilar dos veces",
    "fi": "Voi alkyloitua kahdesti",
    "fr": "Peut alkyler deux fois",
    "he": "יכול alkylate twice",
    "hr": "Može alkilirati dvaput",
    "hu": "Can alkylnále twice",
    "id": "Dapat dialkilasi dua kali",
    "it": "Può alchilare due volte",
    "ja": "2回アルキル化できる",
    "ko": "두 번 알킬화 가능",
    "lv": "Var alk...
Related Reactions

malonic-ester-synthesis

Is Free

false