Hydrochloric Acid → 3-Cyclohexylacrylic acid

HRID 751764

Reaction equation

HRID 751764 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[CH:8]1(C=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl>N1C=CC=CC=1.N1CCCCC1>[CH:8]1([CH:1]=[CH:2][C:3]([OH:5])=[O:4])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 2873483-Cyclohexylacrylic acidYield 107.4%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Procedure

3.34 g (32.1 mmol) of malonic acid are dissolved in pyridine (10 ml), after the weakly exothermic reaction has subsided 3.0 g (26.7 mmol) of cyclohexanecarbaldehyde and 0.23 g (2.7 mmol) of piperidine are added, and the reaction mixture is heated to reflux for 4 h. The cooled reaction solution is added to a mixture of ice and concentrated hydrochloric acid, the aqueous phase is extracted three times with diethyl ether, the combined organic phases are dried over sodium sulfate, filtered, and the solvent is removed in vacuo. 4.42 g of product are obtained, which is reacted further without purification.

Workup

  1. customafter the weakly exothermic reaction
  2. additionare added
  3. temperaturethe reaction mixture is heated
  4. temperatureto reflux for 4 h
  5. customThe cooled reaction solution
  6. extractionthe aqueous phase is extracted three times with diethyl ether
  7. dry with materialthe combined organic phases are dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-8ab3752884e1462380c3b22efcf07523
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Linked notes

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