4-Chloromandelic acid → Methyl 2-(4-chlorophenyl)-2-hydroxyacetate

A 250 mL round bottom flask containing 5.6 g (30 mmol) of p-chlorophenyl-α-hydroxyacetic acid and 100 mL of concentrated HCl:MeOH (1:9) was warmed to reflux for 12 hours. The solution was concentrated under reduced pressure, diluted with 250 mL of Et2O and washed once with 30 mL of H2O, twice with 30 mL of NaHCO3 solution, once with 30 mL of H2O and once with 30 mL of brine. The organic layer was dried (Na2SO4) and concentrated leaving 5.0 g (83%) of methyl p-chlorophenyl-α-hydroxyacetate lit m.p. 55° C.)

1. temperaturewas warmed
2. temperatureto reflux for 12 hours
3. concentrationThe solution was concentrated under reduced pressure
4. additiondiluted with 250 mL of Et2O
5. washwashed once with 30 mL of H2O, twice with 30 mL of NaHCO3 solution, once with 30 mL of H2O and once with 30 mL of brine
6. dry with materialThe organic layer was dried (Na2SO4)
7. concentrationconcentrated

ORD record

ord-f7e36203bcb84ad0a67633b1f0c59d62

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05504108