Sulfuric Acid → 3-phenyl-2(R)-acetoxypropionic acid t-butyl ester

HRID 487865Notes

Reaction equation

HRID 487865 reaction equation
[C:1]1([CH2:7][C@@H:8]([O:12][C:13](=[O:15])[CH3:14])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[CH3:21][C:22](=[CH2:24])[CH3:23].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:22]([O:10][C:9](=[O:11])[C@H:8]([O:12][C:13](=[O:15])[CH3:14])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:24])([CH3:23])[CH3:21]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 11469837(R)-2-acetoxy-3-phenylpropanoic acid

Product 1

HCID 536703193-phenyl-2(R)-acetoxypropionic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cool to -30° to -20° C., 3-phenyl-2(R)-acetoxypropionic acid (10.5 g) in CH2Cl2 (200 mL), add conc. H2SO4 (0.5 mL) and isobutylene (120 mL), seal the vessel, and stir at room temperature for 2 days. Vent the vessel, pour the reaction mixture into NaHCO3 solution, and extract with CH2Cl2. Dry the CH2Cl2 extract (MgSO4), then concentrate in vacuo to give 3-phenyl-2(R)-acetoxypropionic acid t-butyl ester.

Workup

  1. temperatureCool to -30° to -20° C.
  2. customseal the vessel
  3. extractionextract with CH2Cl2
  4. dry with materialDry the CH2Cl2
  5. extractionextract (MgSO4)
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-910d21198aff4873b432f9205abfbbde
Source dataset
uspto-grants-1994_03
Patent number
US05298492

Reaction notes

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