3-Chlorophenol → 2-Phenoxybutanoic acid

HRID 1722045Notes

Reaction equation

HRID 1722045 reaction equation
C[C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+]([O-])=O.ClC1C=C(O)C=CC=1.[C:20]1(=[O:25])[O:24][CH:22]([CH3:23])[CH2:21]1>>[O:11]([CH:21]([CH2:22][CH3:23])[C:20]([OH:25])=[O:24])[C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 79333-ChlorophenolHCID 174123-Methyl-4-nitrophenolHCID 18303beta-BUTYROLACTONE

Product 1

HCID 579872-Phenoxybutanoic acidYield 13%

Procedure

By the two-step method of Preparations G1/G2 and G3/G4, 3-methyl-4-nitrophenol and 3-chlorophenol were reacted with beta-butyrolactone and the intermediate phenoxybutyric acid derivative cyclized to form, respectively, 2,7-dimethyl-6-nitrochroman-4-one [overall yield 13.0%; m.p. 110°-113° C.;

Sources & evidence

ORD record
ord-44962466e56f4742b0c01752cbbe7bcc
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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