Chloroform → 2-(3,4-Dichlorophenyl)acetyl chloride

3,4-Dichlorophenylacetyl chloride is prepared according to the method described in Example 8, using 3,4-dichlorophenylacetic acid (2.62 g, 12.8 mmol) to give a yellow oil which is dissolved in chloroform (15 mL). This solution is refluxed for 9 hours with a solution of (±)-trans-[2-(4-morpholinyl)]cyclohexanol (2.25 g, 12.2 mmol) in chloroform (10 mL) under nitrogen. The solvent is removed in vacuo, and the residue is partitioned between 1M hydrochloric acid (75 mL) and ether (75 mL). The ether layer is separated and the aqueous is washed with more ether (2×30 mL), and then basified to pH14 by the addition of 50% sodium hydroxide solution. This is then extracted with ether (4×30 mL), and the combined ether extracts are washed with water until GC shows no unreacted aminoalcohol in the ether. The ether containing the product is then dried over sodium sulfate, and the solvent is removed to leave the crude free ester. The residue is dissolved in ether (20 mL) and treated with HCl in ether to precipitate the salt. It is washed with ether and recrystallised from hot methanol to yield the title compound.

1. customto give a yellow oil which
2. customThe solvent is removed in vacuo
3. customthe residue is partitioned between 1M hydrochloric acid (75 mL) and ether (75 mL)
4. customThe ether layer is separated
5. washthe aqueous is washed with more ether (2×30 mL)
6. additionbasified to pH14 by the addition of 50% sodium hydroxide solution
7. extractionThis is then extracted with ether (4×30 mL)
8. washthe combined ether extracts are washed with water until GC
9. dry with materialThe ether containing the product is then dried over sodium sulfate
10. customthe solvent is removed
11. customto leave the crude free ester

ORD record

ord-2c7a0904e94b4700b582fc4f9b5cfb40

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05885984