Sulfuric Acid → HCID 11830633, compound

HRID 1647356Notes

Reaction equation

HRID 1647356 reaction equation
[C:1]1([CH2:7][C@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[C:18](OC(=O)C)(=[O:20])[CH3:19].C(OCC)C>C(O)(=O)C>[C:1]1([CH2:7][C@H:8]([O:12][C:18](=[O:20])[CH3:19])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 4447183-Phenyllactic acid, (S)-

Product 1

HCID 11830633HCID 11830633, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Mix (S)-3-phenyllactic acid (11.17g, 67.2mmol) and sulfuric acid (0.3mL of a 10% solution in acetic acid). Add acetic anhydride (6.34mL, 67.2mmol) over 10 minutes. Warm to 90° C. with stirring for 45 minutes. Allow to cool, pour into diethyl ether and wash with water three times. Separate the organic phase, dry (MgSO4) and concentrate in vacuo to yield 13.16g (94%) (S)-3-phenyl-2-acetyloxypropionic acid as a white oil.

Workup

  1. temperatureAllow to cool
  2. washwash with water three times
  3. customSeparate the organic phase
  4. dry with materialdry (MgSO4)
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-8bb80a56211b4fb981635a5b1e6fed74
Source dataset
uspto-grants-1995_07
Patent number
US05430145

Reaction notes

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