Acetic Acid → 4'-Hydroxy-4-biphenylcarboxylic acid

HRID 234555Notes

Reaction equation

HRID 234555 reaction equation
S(=O)(=O)(O)O.O.C(C1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)#N.[C:22]([OH:25])(=[O:24])[CH3:23]>>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:23]([C:22]([OH:25])=[O:24])=[CH:10][CH:11]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Procedure

A mixture of concentrated sulphuric acid (115 ml) and water (115 ml) was added dropwise to a stirred suspension of 4-cyano-4'-hydroxybiphenyl 39 (25.62 g, 131.4 mmol) in glacial acetic acid (400 ml). The mixture was heated under reflux for 48 hours, the cooled reaction mixture was then poured into water (600 ml) with stirring and the white precipitate filtered off. The aqueous filtrate was then washed with diethyl ether (4×70 ml); the combined extracts were then washed with water (50 ml), dried (MgSO4) filtered and evaporated to give a white solid, both crops of product were combined, dried thoroughly and recrystallised (glacial acetic acid) and dried in vacuo (P2O5, 0.30 mm Hg, 50° C., 5 hours).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 48 hours
  3. customthe cooled reaction mixture
  4. filtrationthe white precipitate filtered off
  5. washThe aqueous filtrate was then washed with diethyl ether (4×70 ml)
  6. washthe combined extracts were then washed with water (50 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto give a white solid
  11. customdried thoroughly
  12. customrecrystallised (glacial acetic acid)
  13. dry with materialdried in vacuo (P2O5, 0.30 mm Hg, 50° C., 5 hours)

Sources & evidence

ORD record
ord-2ab8363c12684a60ab978844d4e97c09
Source dataset
uspto-grants-1997_01
Patent number
US05595682

Reaction notes

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