Sodium borohydride → 4-(1-Octynyl)benzyl alcohol

HRID 255999Notes

Reaction equation

HRID 255999 reaction equation
[C:1]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[BH4-].[Na+]>C(O)C>[C:1]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:15][CH:16]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 136885034-(Oct-1-yn-1-yl)benzaldehyde

Product 1

HCID 158812404-(1-Octynyl)benzyl alcoholYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4-(1-octynyl)benzaldehyde (15 g, 0.07 mole from example 4) in ethanol (200 ml) was added sodium borohydride (1.32 g, 0.035 mole) in ethanol and the mixture was stirred for 5 minutes until no further aldehyde remained. The solution was concentrated, ether was added and the solution was washed with water and dried (MgSO4). Evaporation gave an oil which was chromatographed on silica eluting with dichloromethane to give 12.5 g (82%) of the alcohol as an oil, νmax (film) 815, 840, 1020, 1040, 1510, 2220, 3300 cm-1 ; δ(CDCl3) 0.88 (3H, distorted t, terminal CH3), 1.1-1.8 (8H, m, alkylene chain), 2.2 (1H exchangeable, OH), 2.36 (2H, t, J 7 Hz, CH2 --C≡C), 4.56 (2H, s, CH2O), 7.3 (4H, ABq, aromatics). M+ 216.1524 (C15H20O requires, 216.1514).

Workup

  1. concentrationThe solution was concentrated
  2. additionether was added
  3. washthe solution was washed with water
  4. dry with materialdried (MgSO4)
  5. customEvaporation
  6. customgave an oil which
  7. customwas chromatographed on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-81610da3a46c476cba470c6343b60205
Source dataset
uspto-grants-1987_10
Patent number
US04699995

Reaction notes

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