Phenylacetic Acid → Phenylacetyl chloride

Phenylacetyl chloride is prepared according to the method described in Example 8 using phenylacetic acid (2.13 g, 15.6 mmol) to give a pale yellow oil which is dissolved in chloroform (10 mL). This solution is refluxed for 12 hours with a solution of (±)-trans-[2-(4-morpholinyl)]cyclohexanol (2.75 g, 14.9 mmol) in chloroform (10 mL) under nitrogen. The reaction mixture is partitioned between 1M sodium hydroxide solution (100 mL) and dichloromethane (80 mL). The organic layer is separated and the aqueous is washed with more dichloromethane (2×50 mL). The combined dichloromethane extracts are dried over sodium sulfate, and the solvent is removed to leave the crude free ester. This is purified by column chromatography and converted to the hydrochloride salt as described in Example 9. The product is recrystallised from hot methanol to yield the title compound.

1. customto give a pale yellow oil which
2. customThe reaction mixture is partitioned between 1M sodium hydroxide solution (100 mL) and dichloromethane (80 mL)
3. customThe organic layer is separated
4. washthe aqueous is washed with more dichloromethane (2×50 mL)
5. dry with materialThe combined dichloromethane extracts are dried over sodium sulfate
6. customthe solvent is removed
7. customto leave the crude free ester

ORD record

ord-8b9f7c4a15924d71b22590e42b787164

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174879B1