Acetone → p-Bromobenzhydryl alcohol

HRID 1180443

Reaction equation

HRID 1180443 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+].CC(C)=O>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[OH:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 70304-BromobenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 98221p-Bromobenzhydryl alcohol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-bromophenyl)(phenyl)methanone (200 g, 0.766 mole) in THF (600 mL) and methanol (400 mL) was added in portions pulverized sodium borohydride (29 g, 0.766 mole) while maintaining the internal temperature between 3° C. and 10° C. After stirring for an additional 15 minutes, acetone (125 mL) was added and the mixture stirred for a subsequent 10 minutes. The solution was concentrated and the residue partitioned between water (250 mL) and ethyl acetate (1.0 L). The organic layer was separated, dried (Na2SO4), filtered and concentrated. The residue was pumped on by high vacuum for 18 hours to give the title compound as an oil.

Workup

  1. temperaturewhile maintaining the internal temperature between 3° C. and 10° C
  2. stirringthe mixture stirred for a subsequent 10 minutes
  3. concentrationThe solution was concentrated
  4. customthe residue partitioned between water (250 mL) and ethyl acetate (1.0 L)
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. waitThe residue was pumped on by high vacuum for 18 hours

Sources & evidence

ORD record
ord-06e9cc34d79942c1949cf0c986e7f05f
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Linked notes

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