Hydrochloric Acid → Methyl 4-formylcyclohexane-1-carboxylate

HRID 2241791Notes

Reaction equation

HRID 2241791 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1.Cl.CCCCCC>C1COCC1>[CH:3]([CH:4]1[CH2:5][CH2:6][CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:9]1)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 59133005HCID 59133005, compound

Product 1

HCID 11252253Methyl 4-formylcyclohexane-1-carboxylateYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

103 g of methyl 4-methoxymethylidenecyclohexanecarboxylate was dissolved in 350 mL of THF and 100 mL of 10% hydrochloric acid was added dropwise at 11 to 13° C. over 10 minutes. After stirring at room temperature for 3 hours, 80 mL of hexane was added. The aqueous layer was extracted with ethyl acetate and then combined with the organic layer, followed by washing in turn with water and saturated saline. The mixture was dried over anhydrous sodium sulfate and concentrated to obtain 92.4 g of methyl 4-formylcyclohexanecarboxylate as an oily substance. The gas chromatography analysis revealed that the resulting substance is a mixture of a cis isomer and a trans isomer in a mixing ratio of 64:36.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washby washing in turn with water and saturated saline
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f4cd204983fb49668dac22bb9a715352
Source dataset
uspto-grants-2010_03
Patent number
US07670504B2

Reaction notes

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