Methanol → methyl (2R)-2-hydroxy-3-phenylpropanoate

HRID 7802Notes

Reaction equation

HRID 7802 reaction equation
[OH:1][C@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[CH3:18]O>C(OCC)C>[CH3:18][O:4][C:3](=[O:5])[C@H:2]([OH:1])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 643327(R)-3-phenyllactic acid

Product 1

HCID 10986876methyl (2R)-2-hydroxy-3-phenylpropanoateYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-2-hydroxy-3-phenylpropionic acid (1.5 g, 12.9 mol) in methanol (18 mL) at 0° C. was added concentrated sulfuric acid (0.2 mL). The reaction mixture was stirred at 0° C. for 30 min and warmed to room temperature for 24 h. Concentration in vacuo gave a residue which was diluted with diethyl ether (200 mL) and washed with water, saturated sodium bicarbonate and brine. The organic layer was separated, dried with sodium sulfate, filtered and concentrated in vacuo giving a white solid 1.62 g (85%), which was used without further purification.

Workup

  1. temperaturewarmed to room temperature for 24 h
  2. concentrationConcentration in vacuo
  3. customgave a residue which
  4. washwashed with water, saturated sodium bicarbonate and brine
  5. customThe organic layer was separated
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d4e1bbe08d4416ebf8a9bbeacc66b58
Source dataset
uspto-grants-2006_08
Patent number
US07087622B2

Reaction notes

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