Diethyl Ether → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenol

HRID 1074479Notes

Reaction equation

HRID 1074479 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[BH4-].[Na+].[Cl-].[Na+].CCOCC>CO>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][CH:18]([OH:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 127882083-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenone

Product 1

HCID 127882863-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a -18° C. solution of 70.0 g (0.20 mol) of 3-[4-(1,1-dimethylheptyl]-2-hydroxyphenyl]-cyclohex-2-enone in 200 ml of methanol is added 7.6 g (0.20 mol) of sodium borohydride. The reaction mixture is stirred for 30 minutes and then added to one liter of saturated sodium chloride-one liter of ether. The ether extract is washed once with 500 ml of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 500 g of silica gel eluted with 50% ether-pentane to yield the title compound.

Workup

  1. extractionThe ether extract
  2. washis washed once with 500 ml of saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is purified via column chromatography on 500 g of silica gel
  6. washeluted with 50% ether-pentane

Sources & evidence

ORD record
ord-a6dc9624671147fa93d582dfe52119a6
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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