4-Chlorophenol → 4-(5-Chloro-2-hydroxyphenyl)-4-oxobutanoic acid

HRID 1763334Notes

Reaction equation

HRID 1763334 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH2:11][CH2:10]1.[Cl-].[Al+3].[Cl-].[Cl-]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:3]=1)[C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:15]

Participants

4

Reactant 3

HCID 46844-ChlorophenolHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 41452424-(5-Chloro-2-hydroxyphenyl)-4-oxobutanoic acidYield 49%

Procedure

4-Chlorphenol was reacted with succinic anhydride and aluminium chloride in a similar manner to the procedure described in Example 8 (i) to give 3-(5-chloro-2-hydroxybenzoyl)propionic acid (49%, m.p. 172°-173° C). (Found: M+, 228/230. C10H9Cl O4 requires: M, 228/230). (ii) 3-(5-Chloro-2-hydroxybenzoyl)propionic acid was esterified with methanol-hydrogen chloride in a similar manner to the procedure described in Example 1 (i) to give methyl 3-(3-chloro-2-hydroxybenzoyl)propionate (75%).

Sources & evidence

ORD record
ord-b1c7b1ce291449268ef5a3b63d53fcb1
Source dataset
uspto-grants-1978_09
Patent number
US04111936

Reaction notes

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