Diethyl Ether → 1,1-Diphenyl-3-bromopropan-2-ol

HRID 436941Notes

Reaction equation

HRID 436941 reaction equation
[BH4-].[Na+].[C:3]1([CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:13])[CH2:11][Br:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCOCC>[OH-].[Na+].CO>[C:3]1([CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]([OH:13])[CH2:11][Br:12])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 27946353-Bromo-1,1-diphenylacetoneHCID 4311764Sodium borohydride

Product 1

HCID 125490671,1-Diphenyl-3-bromopropan-2-olYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Sodium borohydride (1 52 g.) in sodium hydroxide solution (15 ml. 0.02M) was added to 1,1-diphenyl-3-bromo-propan-2-one (12 g.) in methanol (50 ml.), and the solution was stirred for one hour. Isolation through ether in the usual manner afforded 1,1-diphenyl-3-bromo-propan-2-ol (10 4 g. 86%) as an oil.

Sources & evidence

ORD record
ord-a9f793690624471d99e6cfcd3a65c5a8
Source dataset
uspto-grants-1977_06
Patent number
US04028415

Reaction notes

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