2-(2-Fluorobiphenyl-4-yl)-2-hydroxypropanoic acid → 2-(2-Fluoro-4-biphenylyl)acrylic acid

HRID 1659643Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([C:8](O)([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>O>[F:1][C:2]1[CH:7]=[C:6]([C:8](=[CH2:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product of Example 1 (2 g.) was mixed with polyphosphoric acid (10 g.) and heated at 100° C. for 30 minutes. Water was added and the mixture stirred and extracted with ether. The extract was dried, filtered and evaporated to give crude 2-(2-fluoro-4-biphenylyl)acrylic acid in a yield of 91%, m.p. 169°-172° C. This was recrystallised from a mixture of ether and light petroleum (b.p. 40°-60° C.) to give pure material, m.p. 176°-177° C.

Workup

extractionextracted with ether
customThe extract was dried
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-2b865447f41f41e18de56d104a3b176b
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04304931

Reaction notes

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