Sulfuric Acid → HCID 11830633, compound

HRID 1721022Notes

Reaction equation

HRID 1721022 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-9600d576579848fc98e921b149b08c1b
Source dataset
uspto-grants-1996_04
Patent number
US05508411

Reaction notes

Loading…