Sulfuric Acid → Methyl 2-oxo-3-phenylpropanoate

HRID 1252363Notes

Reaction equation

HRID 1252363 reaction equation
S(=O)(=O)(O)O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:18]1([CH2:24][C:25](=[O:33])[C:26]([O:28][CH2:29]CCC)=[O:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC1C=CC=CC=1C>[C:18]1([CH2:24][C:25](=[O:33])[C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 18979724Butyl phenylpyruvate

Product 1

HCID 562359Methyl 2-oxo-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Following the procedure of step (iii) of Example 1 but charging 1 g of sulfuric acid into the three-necked flask in lieu of p-toluenesulfonic acid monohydrate, and the whole o-xylene solution containing 95 g (0.43 mole) of butyl phenylpyruvate and sulfuric acid as obtained in step (ii) of Example 8 into the dropping funnel in place of methyl phenylpyruvate, the reaction was carried out in the same manner as in step (iii) of Example 1. The total reaction time was prolonged to 6 hours. The conversion of butyl phenylpyruvate was 97 percent and the selectivity toward butyl α-acetamidocinnamate 85 mole percent (yield of butyl α-acetamidocinnamate: 93 g). The reaction mixture was washed with water in the same manner as in step (iii) of Example 1 to give about 650 ml of an o-xylene solution containing butyl α-acetamidocinnamate in a concentration of about 0.55 mole per liter.

Sources & evidence

ORD record
ord-a13ffb120bc5464c8ce0b259a06ae5bb
Source dataset
uspto-grants-1988_05
Patent number
US04743547

Reaction notes

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