Sodium Bicarbonate → 4-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-butanol

HRID 894906Notes

Reaction equation

HRID 894906 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][CH:26]([OH: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][CH:26]([OH: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 205179964-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanolHCID 178418361HCID 178418361, compound

Product 1

HCID 205179974-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-butanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 390 mg. (1.02 mmols.) of 4-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanol, 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 for 20 minutes. The reaction mixture is filtered through diatomaceous earth with ethyl acetate and evaporated to an oil. The oil is purified via rapid column chromatography on silica gel eluted with ether to give a quantitative yield of the title compound as an oil.

Workup

  1. additionA mixture of 390 mg
  2. filtrationThe reaction mixture is filtered through diatomaceous earth with ethyl acetate
  3. customevaporated to an oil
  4. customThe oil is purified via rapid column chromatography on silica gel
  5. washeluted with ether

Sources & evidence

ORD record
ord-878c3eb4a9ba42e28aee5ab49987adb9
Source dataset
uspto-grants-1981_08
Patent number
US04284829

Reaction notes

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