Sulfuric Acid → HCID 11830633, compound

HRID 260321Notes

Reaction equation

HRID 260321 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 (11.17 g, 67.2 mmol) and sulfuric acid (0.3 mL of a 10% solution in acetic acid). Add acetic anhydride (6.34 mL, 67.2 mmol) 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 13.16 g (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-96c719ad27d84f89a2a1c2049bf2976c
Source dataset
uspto-grants-1996_06
Patent number
US05527795

Reaction notes

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