Acetic Acid → (1,1'-Biphenyl)-4-butanoic acid, gamma-hydroxy-

HRID 1856512

Reaction equation

HRID 1856512 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:3][CH:2]=1.[OH-].[Na+].[BH4-].[Na+].C(O)(=O)C>O>[OH:8][CH:7]([C:4]1[CH:5]=[CH:6][C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:2][CH:3]=1)[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3335FenbufenHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride

Product 1

HCID 16072199(1,1'-Biphenyl)-4-butanoic acid, gamma-hydroxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 25.4 g. portion of 3-(4-biphenylylcarbonyl)propionic acid is dissolved in 2 liters of water made alkaline with sodium hydroxide. A 37.8 g. portion of sodium borohydride is added and the mixture is stirred for 2 hours. The suspension is then slowly poured into 100 ml. of glacial acetic acid. The mixture is cooled and the resulting solid is filtered, washed with water and dried giving the desired product, m.p. 139°-140° C.

Workup

  1. additionThe suspension is then slowly poured into 100 ml
  2. temperatureThe mixture is cooled
  3. filtrationthe resulting solid is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-683b6ab37ab6474ab8171af01f918ae9
Source dataset
uspto-grants-1980_08
Patent number
US04219668

Linked notes

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