Methanol → 4-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanol

HRID 894419Notes

Reaction equation

HRID 894419 reaction equation
[CH2:1]([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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+].[Cl-].[Na+]>CCOCC>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:22])([CH3:23])[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])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 128821654-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone

Product 1

HCID 205179964-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanolYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a -15° C. solution of 0.5 g. (1.31 mmols.) of 4-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone (the product of Example 1) in 5 ml. of methanol is added 50 mg. (1.31 mmols.) of sodium borohydride. The reaction mixture is stirred for 30 minutes and is then added to 100 ml. of saturated sodium chloride-150 ml. ether. The ether extract is washed once with 100 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil is purified via column chromatography on 100 g. of silica gel eluted with 1:1 ether:cyclohexane to yield 419 mg. (84%) of the title compound as an oil.

Workup

  1. customTo a -15° C.
  2. additionis then added to 100 ml
  3. extractionThe ether extract
  4. washis washed once with 100 ml
  5. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  6. customevaporated to an oil
  7. customThe oil is purified via column chromatography on 100 g
  8. washof silica gel eluted with 1:1 ether
  9. customcyclohexane to yield 419 mg

Sources & evidence

ORD record
ord-e8a4ffd9918740c59ad908801c3717b6
Source dataset
uspto-grants-1981_08
Patent number
US04283569

Reaction notes

Loading…