Sodium Bicarbonate → 4-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone

HRID 894418Notes

Reaction equation

HRID 894418 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH2:24][CH2:25][C:26](=[O:28])[CH3:27])C1C=CC=CC=1.C(=O)(O)[O-].[Na+].[H][H]>[Pd].C(O)C>[CH3:23][C:15]([C:13]1[CH:12]=[CH:11][C:10]([CH2:24][CH2:25][C:26](=[O:28])[CH3:27])=[C:9]([OH:8])[CH:14]=1)([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 128821654-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 128821664-[2-Hydroxy-4-(1,1-dimethylheptyl)phenyl]-2-butanoneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.5 g. (1.31 mmols.) of 4-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone, 360 mg. of solid sodium bicarbonate, 100 mg. of 10% palladium-on-carbon and 10 ml. of ethanol is stirred under one atmosphere of hydrogen pressure for one hour. The reaction mixture is filtered through diatomaceous earth with ethyl acetate and the filtrate evaporated to an oil. The oil is purified via column chromatography on 100 g. of silica gel eluted with 50% ether-cyclohexane to yield 247 mg. (93%) of the title compound as an oil.

Workup

  1. additionA mixture of 0.5 g
  2. filtrationThe reaction mixture is filtered through diatomaceous earth with ethyl acetate
  3. customthe filtrate evaporated to an oil
  4. customThe oil is purified via column chromatography on 100 g
  5. washof silica gel eluted with 50% ether-cyclohexane
  6. customto yield 247 mg

Sources & evidence

ORD record
ord-c0bfab1b92e94c628661145276a1e669
Source dataset
uspto-grants-1981_08
Patent number
US04283569

Reaction notes

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