Formic Acid → HCID 178497880, compound

HRID 1681798Notes

Reaction equation

HRID 1681798 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.C1(C)C=CC=CC=1.C(O)=O.[OH-].[K+]>CO>[CH:3]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=2)[CH2:6][CH2:5]1)=[O:2]

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 methyl 4-[4-(methoxymethyl idene)-cyclohexyl]benzoate, 1 l 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 cis/trans mixture obtained was dissolved in 600 ml of methanol. The solution was added dropwise while gassing with nitrogen at 3° C. within 10 minutes to 1.2 l of a 0.1N methanolic potassium hydroxide solution. 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 gave 88.5 g of methyl 4-(trans-4-formylcyclohexyl)-benzoate 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. customobtained
  7. additionThe solution was added dropwise
  8. stirringThe reaction mixture was stirred at 3° C. for a further 1 hour
  9. extractionextracted with diethyl ether
  10. washThe organic phases were washed neutral with water
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customRecrystallization of the residue from tert.butyl methyl ether

Sources & evidence

ORD record
ord-b1536bab87b84568a781c292ae959ac4
Source dataset
uspto-grants-1992_12
Patent number
US05174921

Reaction notes

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