4-BENZYLOXY-3-CHLORO-BENZOIC ACID synthesis
- Product Name:4-BENZYLOXY-3-CHLORO-BENZOIC ACID
- CAS Number:106931-79-7
- Molecular formula:C14H11ClO3
- Molecular Weight:262.69
536974-86-4
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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
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