Sodium Hydroxide → HCID 20303502, compound

HRID 1732998Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 54196653HCID 54196653, compound

Product 1

HCID 20303502HCID 20303502, compoundYield 95%

Procedure

4.4 g (17.7 mmoles) of 4-(4-fluoropyrazol-1-yl)phenylacetic acid ethyl ester in 60 ml of 1 N solution of sodium hydroxide are heated to 100° C. for 2 hours. After cooling and extraction with benzene, clarification (effected with activated charcoal) is followed by acidification with concentrated hydrochloric acid to produce 3.7 g (95% of theory) of 4-(4-fluoropyrazol-1-yl)phenylacetic acid, m.p. 165° to 167° C. (from acetonitrile).

Workup

temperatureAfter cooling
extractionextraction with benzene, clarification (effected with activated charcoal)

Sources & evidence

ORD record: ord-94f89f7e3608499da44292dc5a8d4c24
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04239901

Reaction notes

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