3-Phenylmethoxypropanoic acid chloride synthesis
- Product Name:3-Phenylmethoxypropanoic acid chloride
- CAS Number:4244-66-0
- Molecular formula:C10H11ClO2
- Molecular Weight:198.65
27912-85-2
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Yield:4244-66-0 100%
Reaction Conditions:
with oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at 0 - 20; for 1.5 h;Inert atmosphere;
Steps:
1 Preparation of 3-(benzyloxy)propanoyl chloride, (15).
An oven-dried, 1.0 L round- bottomed flask equipped with rubber septum containing thermometer, nitrogen inlet and outlet, cooling bath, and magnetic stirrer, was charged with 3-(benzyloxy)propanoic acid (14) (27.5 g, 0.153 mol) and anhydrous DCM (500 mL). The solution was cooled to 0-5 °C (internal temperature) using an ice-water bath. Oxalyl chloride (25.8 mL, 0.305 mol) was then added dropwise over 10 min under nitrogen atmosphere. After 15 min at 0-5 °C, anhydrous DMF (0.75 mL) was added dropwise over 15 min. After 15 min, the ice bath was removed and the reaction warmed to room temperature. After 1 h at ambient temperature, the mixture was concentrated under reduced pressure using a 30 °C water bath, it was then co-evaporated with anhydrous DCM (3 x 100 mL), and dried under reduced pressure using a 35 °C water bath for 1.0 h, which generated (15) (30.32 g, quantitative yield) as a pinkish-orange color solid. This was used in the next step without further purification.
References:
WO2022/82305,2022,A1 Location in patent:Paragraph 00303-00304; 00322-00323
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4799-68-2
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