2-Propenoic acid, 3-phenyl- → Coumarin

HRID 1973702Notes

Reaction equation

HRID 1973702 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3](O)[CH:2]=1.[O-2].[O-2].[O-2].[Al+3].[Al+3].C(O)(=O)C=CC1C=CC=CC=1>[Pt].C(O)(=O)C>[O:10]1[C:5]2[C:6](=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:7]=[CH:8][C:9]1=[O:11]

Participants

6

Reactant 3

HCID 87842-Propenoic acid, 3-phenyl-HCID 637542P-Coumaric AcidHCID 9989226Alumina

Product 1

HCID 323Coumarin

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred glass reactor is added 10 mmoles of coumaric acid, 0.5 mmoles of platinum composited on a gamma-alumina support and 60 grams of acetic acid. The reactor is heated to a temperature of 100° C. by means of an oil bath while effecting the reaction in a nitrogen atmosphere. At the end of 4 hours, it will be found that a major portion of the cinnamic acid is cyclized to form coumarin.

Workup

  1. customthe reaction in a nitrogen atmosphere
  2. customAt the end of 4 hours, it

Sources & evidence

ORD record
ord-7d8fa282fed947a0814dfe8ca0edde0a
Source dataset
uspto-grants-1976_12
Patent number
US03998851

Reaction notes

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