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

HRID 1053605Notes

Reaction equation

HRID 1053605 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-6508dbc1be154d08bb7661b8aa764d13
Source dataset
uspto-grants-2016_07
Patent number
US09394239B2

Reaction notes

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