Acetic Anhydride → 2-Acetoxy-2-(2-fluoro-4-biphenylyl)propionic acid

HRID 1449050Notes

Reaction equation

HRID 1449050 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:13])([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>O>[C:20]([O:13][C:8]([C:6]1[CH:5]=[CH:4][C:3]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:2]([F:1])[CH:7]=1)([CH3:12])[C:9]([OH:11])=[O:10])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 233109062-(2-Fluorobiphenyl-4-yl)-2-hydroxypropanoic acid

Product 1

HCID 205597762-Acetoxy-2-(2-fluoro-4-biphenylyl)propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from Example 1 (5 g.) was added to acetic anhydride (50 ml.) and the mixture heated on a steam bath for 2 hours after the acid had all dissolved. The mixture was then cooled and poured into water (200 ml.). The aqueous mixture was allowed to stand for 2 hours and the product collected recrystallised from a mixture of ether and light petroleum (b.p. 62°-68° C.) to give 2-acetoxy-2-(2-fluoro-4-biphenylyl)propionic acid, m.p. 141°-142° C.

Workup

  1. temperaturethe mixture heated on a steam bath for 2 hours after the acid
  2. temperatureThe mixture was then cooled
  3. customthe product collected
  4. customrecrystallised from a mixture of ether and light petroleum (b.p. 62°-68° C.)

Sources & evidence

ORD record
ord-95036ab80bd742b198589c275c02fd27
Source dataset
uspto-grants-1980_02
Patent number
US04188491

Reaction notes

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