Methyl Acrylate → 6-bromo-3,4-dihydro-2H-1-benzopyran-4-one

HRID 464745Notes

Reaction equation

HRID 464745 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](OC)(=[O:12])[CH:10]=[CH2:11].BrC1C=CC(OC(C)C(O)=O)=CC=1>CO.S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:8][CH2:11][CH2:10][C:9]2=[O:12]

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 78084-BromophenolHCID 35075932-(4-bromophenoxy)propanoic acid

Product 1

HCID 41974516-bromo-3,4-dihydro-2H-1-benzopyran-4-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

The title compound was prepared by the method of Canalini et al.2 by the reaction of 4-bromophenol (40 g, 0.23 mole) and methyl acrylate (100 ml) in the presence of Triton B (6 ml of a 40% solution in methanol); followed by dilute acid hydrolysis of the resulting ester and cyclisation of the (4-bromophenoxy)propionic acid in concentrated sulphuric acid. The product was recrystallised from petroleum ether (60°-80° C.) to give a white crystalline solid (6.80 g, 13%). M.p. 78°-80° C.

Workup

  1. additionby dilute
  2. customThe product was recrystallised from petroleum ether (60°-80° C.)

Sources & evidence

ORD record
ord-ae529965070f41b6a10a3d9d6568a3a4
Source dataset
uspto-grants-1985_10
Patent number
US04548948

Reaction notes

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