Sulfuric Acid → Methyl 2-[(acetyloxy)methyl]-3-phenylprop-2-enoate

HRID 1066451

Reaction equation

HRID 1066451 reaction equation
O[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].[C:15]([O:18]C(=O)C)(=[O:17])[CH3:16].S(=O)(=O)(O)O>>[CH:2](=[C:3]([CH2:8][O:18][C:15](=[O:17])[CH3:16])[C:4]([O:6][CH3:7])=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 9942369Methyl 3-Hydroxy-2-methylene-3-phenylpropionate

Product 1

HCID 53678280Methyl 2-[(acetyloxy)methyl]-3-phenylprop-2-enoateYield 108.5%

Conditions

Temperature
100 °C

Procedure

Methyl 3-hydroxy-2-methylene-3-phenylpropionate [formula (III), R1=Ph, R2=Me, 108.8 g] obtained in Examplel was dissolved in 113 ml (1.20 mols) of acetic anhydride, and 0.2 ml of sulfuric acid were added thereto. The resulting mixture was stirred at 100° C. for 4 hours. After the completion of the reaction, the reaction solution was concentrated under reduced pressure to obtain 143.9 g of a crude product of the above title compound. The 1H-NMR spectrum of this product revealed that the resulting compound was a mixture of E-form and Z-form (87:13).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e378d349fe6343f396a4a9ec78cc4a2f
Source dataset
uspto-grants-2001_06
Patent number
US06242635B1

Linked notes

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