Epichlorohydrin → 4-(2,3-Epoxypropoxy)salicylic acid methyl ester

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11].[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:6][C:7]([O:10][CH2:13][CH:15]2[O:17][CH2:16]2)=[CH:8][CH:9]=1)[OH:11]

Participants

Reactant 3

HCID 7835Epichlorohydrin

HCID 11430Potassium Carbonate

HCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 126113354-(2,3-Epoxypropoxy)salicylic acid methyl ester

Procedure

By refluxing 34 g of 2,4-dihydroxybenzoic acid methyl ester with 185 g of epichlorohydrin and 35 g of potassium carbonate for 2 to 3 hours, and chromatographing the crude product on 100 g of silica gel (elution with toluene), 4-(2,3-epoxypropoxy)salicylic acid methyl ester having a melting point of 53°-55° is obtained.

Sources & evidence

ORD record: ord-04f489d6f4b84e0caced2494d503c25d
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04727067

Reaction notes

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