Formic Acid → HCID 178497880, compound

HRID 2081523Notes

Reaction equation

HRID 2081523 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][C:13](=[CH:16][O:17]C)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C1(C)C=CC=CC=1.C(O)=O.[OH-].[K+]>CO>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH:16]=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 1140TolueneHCID 14797Potassium HydroxideHCID 19803268HCID 19803268, compound

Product 1

HCID 178497880HCID 178497880, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 123 g of 4-[4-(methoxymethylidene)cyclohexyl]benzoic acid methyl ester 1000 ml of toluene and 500 ml of formic acid was stirred vigorously at room temperature overnight. The formic acid phase was separated. The toluene phase was washed neutral with water, dried over sodium sulfate, filtered and concentrated. The crude trans/cis-mixture obtained was dissolved in 600 ml of methanol. The solution was added dropwise at 3° C. within 10 minutes to 1.2 1 of 0.1N methanolic potassium hydroxide solution while gassing with nitrogen. The reaction mixture was stirred at 3° C. for a further 1 hour, then poured on to ice/water and extracted with diethyl ether. The organic phases were washed neutral with water, dried over sodium sulfate, filtered and concentrated. Recrystallization of the residue from tert. butyl methyl ether yielded 88.5 g of 4-(trans-4-formylcyclohexyl)benzoic acid methyl ester with m.p. 84°-85° C.

Workup

  1. customThe formic acid phase was separated
  2. washThe toluene phase was washed neutral with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude trans/cis-mixture obtained
  7. stirringThe reaction mixture was stirred at 3° C. for a further 1 hour
  8. extractionextracted with diethyl ether
  9. washThe organic phases were washed neutral with water
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customRecrystallization of the residue from tert. butyl methyl ether

Sources & evidence

ORD record
ord-b1d8aeb1f1844394a0f83b29610cebed
Source dataset
uspto-grants-1993_02
Patent number
US05185098

Reaction notes

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