Hydrochloric Acid → Methyl (R)-2-(4-hydroxyphenoxy)propionate

HRID 2392913Notes

Reaction equation

HRID 2392913 reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][C@H:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)(=O)C.Cl>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:9][C@H:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54186344Methyl (R)-2-(4-acetoxyphenoxy)propionate

Product 1

HCID 2733752Methyl (R)-2-(4-hydroxyphenoxy)propionateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 45 g (189 mmol) of methyl (R)-2-(4-acetoxyphenoxy)propionate (enantiomeric excess 94-95%), 135 ml of methanol and 2.5 ml of methanol saturated with gaseous hydrogen chloride was refluxed for 5 h and subsequently concentrated. The crude product was purified by distillation at 140° C. under 0.1 mbar. Yield: 96% (94-95% enantiomeric excess).

Workup

  1. temperaturewas refluxed for 5 h
  2. concentrationsubsequently concentrated
  3. distillationThe crude product was purified by distillation at 140° C. under 0.1 mbar

Sources & evidence

ORD record
ord-221fdf92b5cc45bd9fbc54f9021c4ee5
Source dataset
uspto-grants-1998_09
Patent number
US05801272

Reaction notes

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