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

HRID 2199013Notes

Reaction equation

HRID 2199013 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 was stirred under one atmosphere of hydrogen for 20 minutes. The reaction mixture was filtered through diatomaceous earth with ethyl acetate and evaporated to an oil. The oil was 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 was filtered through diatomaceous earth with ethyl acetate
  3. customevaporated to an oil
  4. customThe oil was purified via rapid column chromatography on silica gel
  5. washeluted with ether

Sources & evidence

ORD record
ord-f3ef2bc9099a45a9baa80840ee7f1355
Source dataset
uspto-grants-1982_11
Patent number
US04360700

Reaction notes

Loading…