Water → 4-(4-Hydroxymethylphenyl)cyclohexanone

HRID 2209766Notes

Reaction equation

HRID 2209766 reaction equation
S(Cl)(Cl)=[O:2].[OH2:5].[NH+]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]1(C)[CH:17]=[CH:16][C:15](S([O-])(=O)=O)=[CH:14][CH:13]=1.N1[CH:28]=[CH:27]C=CC=1>C(OCC)(=O)C.CO.CC(C)=O.[Pd]>[OH:5][CH2:7][C:8]1[CH:28]=[CH:27][C:11]([CH:12]2[CH2:13][CH2:14][C:15](=[O:2])[CH2:16][CH2:17]2)=[CH:10][CH:9]=1

Participants

9

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 193813914-(4-Hydroxymethylphenyl)cyclohexanone

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 180AcetoneSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.5 g of this product in 30 ml of pyridine are combined with 2.2 ml of thionylchloride, whilst cooling with ice. The resulting oil (2.7 g), which is a mixture of two substances, is hydrogenated in a mixture of 40 ml of ethyl acetate and 20 ml of methanol in the presence of 1.5 g of palladium/calcium carbonate at ambient temperature under a hydrogen pressure of 5 bar. The resulting oil (2.4 g) is refluxed overnight in 40 ml of acetone and 10 ml of water with 0.2 g of pyridinium-p-toluenesulphonate. The crude product is purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:1, v:v). 1.0 g of the title compound is obtained, melting point 58°-60° C.

Workup

  1. temperaturewhilst cooling with ice
  2. additiona mixture of two substances
  3. customThe crude product is purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:1, v:v)

Sources & evidence

ORD record
ord-8d806b17d2114cdc8a9721df4591599b
Source dataset
uspto-grants-1995_10
Patent number
US05455273

Reaction notes

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