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

HRID 1449051Notes

Reaction equation

HRID 1449051 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

(+)-2-(2-Fluoro-4-biphenylyl)-2-hydroxypropionic acid (1 g.) from Example 42 was added to acetic anhydride (10 g.) and the mixture stirred overnight at room temperature. The mixture was added to water (40 ml.) and allowed to stand for two hours. The product was collected and 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. 125°-127° C. and [α]D20 -33.0°.

Workup

  1. waitto stand for two hours
  2. customThe product was collected
  3. customrecrystallised from a mixture of ether and light petroleum (b.p. 62°-68° C.)

Sources & evidence

ORD record
ord-a790a65ef6a14c048da6600c38a92f0b
Source dataset
uspto-grants-1980_02
Patent number
US04188491

Reaction notes

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