Hydrochloric Acid → Methyl 4-formylcyclohexane-1-carboxylate

HRID 1674439Notes

Reaction equation

HRID 1674439 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-methoxymethylidene-cyclohexane carboxylate was dissolved in 350 mL of THF, and 100 mL of 10% hydrochloric acid was added dropwise thereto at 11 to 13° C. for 10 minutes. The solution was further stirred at room temperature for 3 hours, and then 80 mL of hexane was added. The aqueous layer was extracted with ethyl acetate, and then the organic layers were combined and washed with water and saturated saline in this order. The resultant product was dried over anhydrous magnesium sulfate, and then concentrated, to obtain 92.4 g of methyl 4-formylcyclohexane carboxylate in the form of an oil-like product. The obtained product was analyzed by gas chromatography, and was found to be a mixture of cis-form:trans-form at a ratio of 64:36.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washwashed with water and saturated saline in this order
  3. dry with materialThe resultant product was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-09da9f63b36b4db8afd1ef839fc38fd1
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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