Formic Acid → HCID 178516011, compound

HRID 486360Notes

Reaction equation

HRID 486360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH:16]3[CH2:25][CH2:24][C:19]4(OCC[O:20]4)[CH2:18][CH2:17]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C(O)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH2:14][CH2:15][CH:16]3[CH2:17][CH2:18][C:19](=[O:20])[CH2:24][CH2:25]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 1140TolueneHCID 178478117HCID 178478117, compound

Product 1

HCID 178516011HCID 178516011, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 31.1 g of 4-chloro-1-[trans-4-[2-(1,4-dioxa-8-spiro[4.5]decyl)ethyl]cyclohexyl]benzene, 207 ml of toluene and 103 ml of formic acid is stirred at room temperature for 1.25 hours while gassing with nitrogen. Thereafter, the reaction mixture is poured into 500 ml of water and extracted with methylene chloride. The organic phases are washed with saturated sodium hydrogen carbonate solution and with water, dried over sodium sulphate and filtered. Concentration of the filtrate gives 4-[2-[trans-4(4-chlorophenyl)cyclohexyl]ethyl]cyclohexanone.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phases are washed with saturated sodium hydrogen carbonate solution and with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-986fcdeaddfe4637a3f8adced6989d28
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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