Acetic Acid → HCID 18470136, compound

HRID 2228903Notes

Reaction equation

HRID 2228903 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:10].[BH4-].[Na+].C(O)(=O)C>O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[OH:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 18470194HCID 18470194, compound

Product 1

HCID 18470136HCID 18470136, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8-bromo-1-(4-chlorophenyl)octan-1-one (0.95 g) in industrial methylated spirit (10 ml) was added sodium borohydride (0.115 g) at −10° C. After stirring for 1 h, glacial acetic acid (0.2 g) was added and the mixture was poured into water (60 ml) and extracted with diethyl ether. The diethyl ether layer was washed with brine and dried over magnesium sulfate. Removal of the solvent under reduced pressure gave an oil that was chromatographed on silica gel using dichloromethane as eluent. This gave 8-bromo-1-(4-chlorophenyl)-1-hydroxyoctane (0.70 g). 1H-NMR (CDCl3) δ 1.15-1.95 (12H, m), 3.40 (2H, t), 4.65 (1H, t) and 7.2-7.4 (4H, m).

Workup

  1. extractionextracted with diethyl ether
  2. washThe diethyl ether layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent under reduced pressure
  5. customgave an oil that
  6. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-ca8638d552934263985cf5b91b00ce69
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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