2-Hydroxy-p-toluic acid → Methyl 2-methoxy-4-methylbenzoate

HRID 1719674Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[C:12]([O-])([O-])=O.[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O>>[CH3:12][O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:23][CH3:24])=[O:5]

Participants

Reactant 3

HCID 57882-Hydroxy-p-toluic acid

HCID 6497Dimethyl Sulfate

HCID 11430Potassium Carbonate

Product 1

HCID 7172021Methyl 2-methoxy-4-methylbenzoate

Procedure

2-Hydroxy-4-methylbenzoic acid was reacted with K2CO3 and dimethyl sulfate to give methyl 2-methoxy-4-methybenzoate (boiling point at 0.7 mm=100° C.). Hydrolysis with 2N sodium hydroxide solution provided 2-methoxy-4-methylbenzoic acid (melting point 103°-104° C.). Bromination to give the 4-bromomethyl compound (melting point 123°-125° C.) and reaction with potassium cyanide provided the 4-cyanomethyl compound (melting point 105°-107° C., from toluene), the catalytic hydrogenation of which with Ra--Ni and reaction with ethanolic hydrochloric acid provided the ethyl 4-(2-aminoethyl)-2-methoxybenzoate hydrochloride (melting point 86°-88° C.).

Sources & evidence

ORD record: ord-932dcab6f81b474d9041461d51b748ed
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04542127

Reaction notes

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