Cyclohexanecarboxaldehyde → 4-(1-Formyl-cyclohexyl)-but-2-enoic acid methyl ester

HRID 2070553

반응식

HRID 2070553 반응식
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][O:10][C:11](=[O:16])[CH:12](O)[CH:13]=[CH2:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:9][O:10][C:11](=[O:16])[CH:12]=[CH:13][CH2:14][C:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 16275CyclohexanecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 545123Methyl 2-hydroxybut-3-enoate

생성물 1

HCID 727655614-(1-Formyl-cyclohexyl)-but-2-enoic acid methyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of cyclohexanecarbaldehyde (6.3 mL) and 2-hydroxy-3-butenoic acid methyl ester (5 mL) in toluene (40 mL) was added para-toluenesulfonic acid monohydrate (20 mg), and the reaction mixture was heated under reflux by using a Dean-Stark apparatus for 16.5 hours. After cooling down to room temperature, the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=50:1 to 10:1) to give 4-(1-formyl-cyclohexyl)-but-2-enoic acid methyl ester (3.7 g).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux
  3. customfor 16.5 hours
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=50:1 to 10:1)

출처 및 근거

ORD 기록
ord-0e9cb1be9eef4ba38d47d16c36ec66cc
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299296B2

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