Thionyl Chloride → 4-Fluorobenzoic Acid

HRID 1586942Notes

Reaction equation

HRID 1586942 reaction equation
CC1(C)CCC(C)(C)C2C=C(N)C=CC1=2.[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.S(Cl)(Cl)=[O:27]>>[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:27])=[O:22])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 678794-Fluorobenzoyl chlorideHCID 114697605,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine

Product 1

HCID 99734-Fluorobenzoic Acid

Procedure

In a manner analogous to Example 9, by reacting 5.9 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine with 4-fluorobenzoyl chloride, obtained from 4 g of 4-fluorobenzoic acid and 15 ml of thionyl chloride, there were obtained, after recrystallization from hexane/ethyl acetate, 6.3 g of p-fluoro-N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)benzamide, m.p. 160°-162° C.

Sources & evidence

ORD record
ord-25e649faaca74f4b8dd06b9bf315e853
Source dataset
uspto-grants-1993_06
Patent number
US05216153

Reaction notes

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