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

HRID 2199012Notes

Reaction equation

HRID 2199012 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 in 5 ml. of methanol was added 50 mg. (1.31 mmols.) of sodium borohydride. The reaction mixture was stirred for 30 minutes and then added to 100 ml. of saturated sodium chloride 150 ml. ether. The ether extract was washed once with 100 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated in an oil. The oil was 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. additionadded to 100 ml
  3. extractionThe ether extract
  4. washwas washed once with 100 ml
  5. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  6. customevaporated in an oil
  7. customThe oil was 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-62cfaf03e38d47f1857a2074cfeed63e
Source dataset
uspto-grants-1982_11
Patent number
US04360700

Reaction notes

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