Ethyl Acetate → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 1624201Notes

Reaction equation

HRID 1624201 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:13](OCC)(=O)C>CO.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:12])[C:9]([O:11][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Product 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetateYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of (R)-2-(3-chlorophenyl)-2-hydroxyacetic acid (25 g, 133.69 mmol, 1.00 equiv.) in methanol (300 mL) and sulfuric acid (3 mL) was heated at reflux for about 16 hours, and then concentrated in vacuo. After the solution was poured into a water/ice mixture (200 mL), the pH value of the solution was adjusted to 9 with sodium carbonate. Standard extractive workup with ethyl acetate (2×100 mL), gave the title product as an off-white solid (24.8 g; yield=93%). 1H NMR (300 MHz, CDCl3) δ: 7.45 (s, 1H), 7.32 (m, 3H), 5.17 (d, J=4.5 Hz, 1H), 3.80 (s, 3H).

Workup

  1. temperatureat reflux for about 16 hours
  2. concentrationconcentrated in vacuo
  3. additionAfter the solution was poured into a water/ice mixture (200 mL)

Sources & evidence

ORD record
ord-ef44bfaea98149bca2875ee49b8b94a5
Source dataset
uspto-grants-2014_07
Patent number
US08778998B2

Reaction notes

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