4-BENZYLOXY-3-CHLORO-BENZOIC ACID synthesis

4synthesis methods

Product Name:4-BENZYLOXY-3-CHLORO-BENZOIC ACID
CAS Number:106931-79-7
Molecular formula:C14H11ClO3
Molecular Weight:262.69

4-BENZYLOXY-3-CHLORO-BENZOIC ACID METHYL ESTER

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Yield:106931-79-7 99%

Reaction Conditions:

Stage #1: 4-benzyloxy-3-chloro-benzoic acid methyl esterwith methanol;sodium hydroxide;water in tetrahydrofuran; for 1 h;
Stage #2: with hydrogenchloride;methanol;water in tetrahydrofuran;

Steps:

16.A

Example 16A4-(benzyloxy)-3-chlorobenzoic acid; 3.0 g (10.84 mmol) methyl 4-(benzyloxy)-3-chlorobenzoate are dissolved in a mixture of 10 ml THF and 10 ml methanol. At rt a solution of 864 mg (21.7 mmol) sodium hydroxide in 10 ml water is added. Stirring is continued for 1 h before the mixture is acidified with IN hydrochloric acid. The white precipitated solid is collected by filtration, washed with water and dried under vacuum (ca. 50⁰C) until weight constancy is observed. The filtrate can be extracted with diethyl ether to yield after evaporation a second batch of pure product. Both batches are combined to afford 2.83 g (99% of th.) of the title compound.LC-MS (method 4): R, = 2.19 min; m/z = 263 (M+H)⁺¹H-NMR (300 MHz, DMSO-d₆): δ = 8.42 (d, IH), 8.38 (dd, IH), 7.55-7.30 (m, 6H), 5.31 (s, 2H).

References:

WO2007/17092,2007,A1 Location in patent:Page/Page column 29