Sulfuric Acid → HCID 11830633, compound

HRID 1441168Notes

Reaction equation

HRID 1441168 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, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Combine (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 extract with water three times. Separate the organic layer, dry (MgSO4) and concentrate in vacuo to yield (S)-3-phenyl-2-acetyloxypropionic acid as a white oil.

Workup

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

Sources & evidence

ORD record
ord-a5f3ff09356a414d8bed3e2adfdad688
Source dataset
uspto-grants-1996_03
Patent number
US05502253

Reaction notes

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