Hexane → Methyl 4-formylcyclohexane-1-carboxylate

HRID 1993145Notes

Reaction equation

HRID 1993145 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.CCCCCC>C1COCC1.Cl>[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 2

HCID 8058HexaneHCID 59133005HCID 59133005, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

103 g of methyl 4-methoxymethylidene-cyclohexane-carboxylate was dissolved in 350 mL of THF, to which 100 mL of 10% hydrochloric acid was added dropwise 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 water phase was extracted with ethyl acetate, and then the organic phases 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. additionwas added dropwise at 11 to 13° C. for 10 minutes
  2. extractionThe water phase was extracted with ethyl acetate
  3. washwashed with water and saturated saline in this order
  4. dry with materialThe resultant product was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-10ffe03360fa4b61a150027350c2e5ab
Source dataset
uspto-grants-2010_01
Patent number
US07651630B2

Reaction notes

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