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

HRID 2070553Notes

Reaction equation

HRID 2070553 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-0e9cb1be9eef4ba38d47d16c36ec66cc
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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