Reaction #2045056

Reaction equation

2-Methoxycarbonylmethoxybenzoic acid methyl ester

2-Methoxycarbonylmethoxy-benzoic acid methyl ester

NaOH

HCl

→

91

Yield 78.2%

2-Carboxymethoxy-benzoic acid

Yield 78.2%

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to room temperature
2. 2
   OtherCrude 91 was purified
3. 3
   workup.DISSOLUTIONby dissolving in 10% aqueous NaOH
4. 4
   Otherprecipitated

Procedure

2-Methoxycarbonylmethoxybenzoic acid methyl ester 1 (95 g, 424 mmol) was added to a 10% aqueous NaOH solution (475 ml) and heated at 80° C. for 4 hrs. The reaction mixture was cooled to room temperature and pH adjusted to 2 with dilute HCl. Crude 91 was purified by dissolving in 10% aqueous NaOH and precipitated by acidifying with HCl, to get pure 91 (65 g, 78.2%) as a white powder. M.p: 189-192° C.

Source