Hydrogen Peroxide → HCID 70600924, compound

HRID 2072229Notes

Reaction equation

HRID 2072229 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:11])([CH3:10])[CH:8]=[CH2:9].[BH4-].[Na+].B(F)(F)F.[OH-:24].[Na+].OO>COCCOCCOC.O>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:11])([CH3:10])[CH2:8][CH2:9][OH:24]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 70600904HCID 70600904, compound

Product 1

HCID 70600924HCID 70600924, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent3×

Procedure

2.24 g. of 3-p-biphenylyl-1-buten-3-ol (obtainable from p-biphenylylmagnesium bromide and methyl vinyl ketone) are dissolved in 5 ml. of diglyme, 3 ml. of a 1 M solution of NaBH4 in diglyme are added and a solution of 0.56 g. of BF3 etherate in 1.2 ml. of diglyme is added dropwise under N2. 0.7 ml. of water is then added and 1.4 ml. of 3N NaOH and 1.4 ml. of 30% H2O2 are then added dropwise at 80°-100°. The mixture is cooled, treated with ice water, and standard working up gives 3-p-biphenylyl-1,3-butanediol, m.p. 115°-117° (the boric acid ester formed as an intermediate being hydrolyzed).

Workup

  1. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-a891cb277d5a4ee6bf1c17f7553690cc
Source dataset
uspto-grants-1977_09
Patent number
US04049823

Reaction notes

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