Octet / Reactions

Malonic Ester Synthesis

Included in Reactions.

Substitution

Source Details

Id

malonic-ester-synthesis

Name
{
  "en": "Malonic Ester Synthesis",
  "ar": "Malonic إستر تحضير",
  "cs": "Malonic Ester Synteza",
  "da": "Malonic Ester Syntese",
  "de": "Malonic Ester Synthese",
  "el": "Malσεic Εστέρας Σύνθεση",
  "es-419": "Síntesis malonique",
  "es-ES": "Síntesis malonique",
  "es": "Síntesis malonique",
  "fi": "Malonic Esteri Synteesi",
  "fr": "Synthèse malonique",
  "he": "Malonic אסטר סינתזה",
  "hr": "Malonic Ester Sinteza",
  "hu": "Malonic Észter Szbantézis",
  "id": "Sintesis Ester Malonat",
  "it": "Sintesi malonique",
  "ja": "マロン酸エステル合成",
  "ko": "말론산 에스터 합성",
  "lv": "Malonic Esteris Sinteze",
  "nb": "Malonic Ester Syntese",
  "nl": "Malonic Ester Synthese",
  "pl": "Malonic Ester Synteza",
  "pt-BR": "Síntese malonique",
  "pt-PT": "Síntese malonique",
  "ro": "Sinteză malonique",
  "ru": "Malonic Эфир Синтез",
  "sk": "Malonic Ester Synteza",
  "sl": "Malonic Ester Sinteza",
  "sv": "Malonic Ester Syntes",
  "th": "การสังเคราะห์เอสเทอร์มาโลนิก",
  "tr": "Malüzerindeic Ester Sentez",
  "uk": "Malonic Естер Синтез",
  "vi": "Tổng hợp malonic ester",
  "zh-Hans": "丙二酸酯合成",
  "zh": "丙二酸酯合成"
}
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)OCC

Product

CCC(=O)O

Reagents

NaOEt, R-X, then H₃O⁺/heat

Mechanism
[
  {
    "smiles": "CCOC(=O)CC(=O)OCC",
    "description": {
      "en": "Diethyl malonate: acidic α-H (pKa ~13)",
      "ar": "Diethyl malonate: حمضي α-H (pKa ~13)",
      "cs": "Diethyl malonate: kysele α-H (pKa ~13)",
      "da": "Diethylmalonat: acidic α-H (pKa ~13)",
      "de": "Diethylmalonat: acidic α-H (pKa ~13)",
      "el": "Diethyl malσεσεe: οξύic α-H (pKa ~13)",
      "es-419": "Dietil malonate: acidic α-H (pKa ~13)",
      "es-ES": "Dietil malonate: acidic α-H (pKa ~13)",
      "es": "Dietil malonate: acidic α-H (pKa ~13)",
      "fi": "Dietyylimalonaatti: acidic α-H (pKa ~13)",
      "fr": "Diéthyle malonate: acidic α-H (pKa ~13)",
      "he": "Diethyl malonate: חומצי α-H (pKa ~13)",
      "hr": "Diethyl malonate: kiseo α-H (pKa ~13)",
      "hu": "Diethyl malonnále: savic α-H (pKa ~13)",
      "id": "Dietil malonat: α-H asam (pKa ~13)",
      "it": "Dietile malonate: acidic α-H (pKa ~13)",
      "ja": "マロン酸ジエチル: 酸性α-H(pKa ~13)",
      "ko": "다이에틸 말로네이트: 산성 α-H(pKa ~13)",
      "lv": "Diethyl malonate: skabs α-H (pKa ~13)",
      "nb": "Dietylmalonat: acidic α-H (pKa ~13)",
      "nl": "Diethylmalonaat: acidic α-H (pKa ~13)",
      "pl": "Diethyl malonate: kwasowy α-H (pKa ~13)",
      "pt-BR": "Dietil malonate: acidic α-H (pKa ~13)",
      "pt-PT": "Dietil malonate: acidic α-H (pKa ~13)",
      "ro": "Dietil malonate: acidic α-H (pKa ~13)",
      "ru": "Diethyl malonate: кислый α-H (pKa ~13)",
      "sk": "Diethyl malonate: kysly α-H (pKa ~13)",
      "sl": "Diethyl malonate: kisel α-H (pKa ~13)",
      "sv": "Dietylmalonat: acidic α-H (pKa ~13)",
      "th": "ไดเอทิลมาโลเนต: α-H เป็นกรด (pKa ~13)",
      "tr": "Diethyl malüzerindedee: olarakitic α-H (pKa ~13)",
      "uk": "Diethyl malonate: кислий α-H (pKa ~13)",
      "vi": "Diethyl malonate: α-H có tính axit (pKa ~13)",
      "zh-Hans": "丙二酸二乙酯:酸性 α-H(pKa ~13)",
      "zh": "丙二酸二乙酯:酸性 α-H(pKa ~13)"
    }
  },
  {
    "smiles": "CCOC(=O)C([C-])C(=O)OCC",
    "description": {
      "en": "Deprotonation gives stabilized enolate",
      "ar": "نزع بروتون يعطي stabilized إينولات",
      "cs": "Deprotonace dava stabilized enolat",
      "da": "Deprotonering giver stabiliseret enolat",
      "de": "Deprotonierung ergibt stabilisiertes Enolat",
      "el": "Deπρωτονίωση δίνει stabilized ενολικό ανιόν",
      "es-419": "Desprotonación da stabilized enolate",
      "es-ES": "Desprotonación da stabilized enolate",
      "es": "Desprotonación da stabilized enolate",
      "fi": "Deprotonointi antaa stabiloidun enolaatin",
      "fr": "Déprotonation donne stabilized enolate",
      "he": "דה-פרוטונציה נותן stabilized אנולאט",
      "hr": "Deprotoniranje daje stabilized enolat",
      "hu": "Deprotonálás ad stabilized enbancslát",
      "id": "Deprotonasi memberi enolat terstabilkan",
      "it": "Deprotonazione dà stabilized enolate",
      "ja": "脱プロトン化で安定化エノラートを与える",
      "ko": "탈양성자화로 안정화된 에놀레이트를 줌",
      "lv": "Deprotonesana dod stabilized enolats",
      "nb": "Deprotonering gir stabilisert enolat",
      "nl": "Deprotonering geeft gestabiliseerd enolaat",
      "pl": "Deprotonacja daje stabilized enolan",
      "pt-BR": "Desprotonação dá stabilized enolate",
      "pt-PT": "Desprotonação dá stabilized enolate",
      "ro": "Deprotonare dă stabilized enolate",
      "ru": "Депротонирование дает stabilized енолят",
      "sk": "Deprotonacia dava stabilized enolat",
      "sl": "Deprotonacija da stabilized enolat",
      "sv": "Deprotonering ger stabiliserat enolat",
      "th": "การดึงโปรตอนออกให้อีโนเลตที่เสถียร",
      "tr": "Deprotüzerindeolarakyüzerinde verir stabilized eyoklde",
      "uk": "Депротонування дає stabilized енолят",
      "vi": "Khử proton cho enolate được bền hóa",
      "zh-Hans": "去质子化得到稳定化烯醇盐",
      "zh": "去质子化得到稳定化烯醇盐"
    }
  },
  {
    "smiles": "CCC(=O)O",
    "description": {
      "en": "After alkylation, hydrolysis, and decarboxylation → carboxylic acid",
      "ar": "After ألكلة, تحلل مائي, و decarboxylation → حمض كربوكسيلي",...
Tips
[
  {
    "en": "Makes substituted acetic acids",
    "ar": "يصنع مستبدل حمض الأسيتيك",
    "cs": "Cini substituovany acetic kyseliny",
    "da": "Makes substitueret acetic acids",
    "de": "Makes substituiert acetic acids",
    "el": "Makes υποκατεστημένο acetic οξύs",
    "es-419": "Forma ácidos acéticos sustituidos",
    "es-ES": "Forma ácidos acéticos sustituidos",
    "es": "Forma ácidos acéticos sustituidos",
    "fi": "Makes substituoitu acetic acids",
    "fr": "Produit des acides acétiques substitués",
    "he": "יוצר מותמר חומצה אצטית",
    "hr": "Cini supstituiran acetic kiseline",
    "hu": "Makes szubsztituált acetic savs",
    "id": "Membuat asam asetat tersubstitusi",
    "it": "Produce acidi acetici sostituiti",
    "ja": "置換酢酸を作る",
    "ko": "치환 아세트산을 만듦",
    "lv": "Padara aizvietots acetic skabes",
    "nb": "Makes substituert acetic acids",
    "nl": "Makes gesubstitueerd acetic acids",
    "pl": "Czyni podstawiony acetic kwasy",
    "pt-BR": "Forma ácidos acéticos substituídos",
    "pt-PT": "Forma ácidos acéticos substituídos",
    "ro": "Formează acizi acetici substituiți",
    "ru": "Делает замещенный acetic кислоты",
    "sk": "Robi substituovany acetic kyseliny",
    "sl": "Naredi substituiran acetic kisline",
    "sv": "Makes substituerad acetic acids",
    "th": "สร้างกรดอะซิติกที่ถูกแทนที่",
    "tr": "Makes sübstitüe acetic olarakits",
    "uk": "Робить заміщений acetic кислоти",
    "vi": "Tạo axit acetic đã thế",
    "zh-Hans": "制备取代乙酸",
    "zh": "制备取代乙酸"
  },
  {
    "en": "Can alkylate twice for disubstituted",
    "ar": "يمكن alkylate twice لـ disubstituted",
    "cs": "Can alkylate twice pro disubstituted",
    "da": "Can alkylate twice for disubstitueret",
    "de": "Can alkylate twice for disubstituiert",
    "el": "Can alkylσεe twice για disubstituted",
    "es-419": "Can alkylate twice para disubstituted",
    "es-ES": "Can alkylate twice para disubstituted",
    "es": "Can alkylate twice para disubstituted",
    "fi": "Can alkylate twice for disubstituoitu",
    "fr": "Can alkylate twice pour disubstituted",
    "he": "יכול alkylate twice עבור disubstituted",
    "hr": "Can alkylate twice za disubstituted",
    "hu": "Can alkylnále twice számára disubstituted",
    "id": "Dapat dialkilasi dua kali untuk disubstitusi",
    "it": "Can alkylate twice per disubstituted",
    "ja": "二置換体にするため2回アルキル化できる",
    "ko": "두 번 알킬화하면 이치환 생성물을 만들 수 있음",
    "lv": "Can alkylate twice prieks disubstituted",
    "nb": "Can alkylate twice for disubstituert",
    "nl": "Can alkylate twice for digesubstitueerd",
    "pl": "Can alkylate twice dla disubstituted",
    "pt-BR": "Can alkylate twice para disubstituted",
    "pt-PT": "Can alkylate twice para disubstituted",
    "ro": "Can alkylate twice pentru disubstituted",
    "ru": "Can alkylate twice для disubstituted",
    "sk": "Can alkylate twice pre disubstituted",
    "sl": "Can alkylate twice za disubstituted",
    "sv": "Can alkylate twice for disubstituerad",
    "th": "ทำแอลคิเลชันได้สองครั้งเพื่อให้ผลิตภัณฑ์แทนที่สองตำแหน่ง",
    "tr": "Can alkyldee twice içiçinde disubstituted",
    "uk": "Can alkylate twice для disubstituted",
    "vi": "Có thể alkyl hóa hai lần để tạo sản phẩm hai thế",
    "zh-Hans": "可烷基化两次得到二取代产物",
    "zh": "可烷基化两次得到二取代产物"
  },
  {
    "en": "Decarboxylation: β-keto acid loses CO₂",
    "ar": "Decarboxylation: β-كيتو حمض loses CO₂",
    "cs": "Decarboxylation: β-keto kyselina loses CO₂",
    "da": "Decarboxylation: β-keto syre loses CO₂",
    "de": "Decarboxylation: β-keto Säure loses CO₂",
    "el": "Decarboxylσεiσε: β-keto οξύ loses CO₂",
    "es-419": "Decarboxylation: β-keto ácido loses CO₂",
    "es-ES": "Decarboxylation: β-keto ácido loses CO₂",
    "es": "Decarboxylation: β-keto ácido loses CO₂",
    "fi": "Decarboxylation: β-keto happo loses CO₂",
    "fr": "Decarboxylation: β-keto acide loses CO₂",
    "he": "Decarboxylation: β-קטו חומצה loses CO₂",
    "hr": "Decarboxylation: β-keto kiselina loses CO₂",
    "hu":...
Related Reactions

acetoacetic-ester-synthesis

Is Free

false