Ammonia → 2-oxo-2H-1-benzopyran-7-yl 4-hydroxybenzoate

HRID 2120515Notes

Reaction equation

HRID 2120515 reaction equation
N.COC([O:6][C:7]1[CH:26]=[CH:25][C:10]([C:11]([O:13][C:14]2[CH:24]=[CH:23][C:17]3[CH:18]=[CH:19][C:20](=[O:22])[O:21][C:16]=3[CH:15]=2)=[O:12])=[CH:9][CH:8]=1)=O>C(O)C>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([O:13][C:14]2[CH:24]=[CH:23][C:17]3[CH:18]=[CH:19][C:20](=[O:22])[O:21][C:16]=3[CH:15]=2)=[O:12])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 234351152-oxo-2H-1-benzopyran-7-yl 4-methoxycarbonyloxybenzoate

Product 1

HCID 234351162-oxo-2H-1-benzopyran-7-yl 4-hydroxybenzoateYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 ml of saturated ethanolic ammonia solution is added dropwise to a solution of 12.2 g of 2-oxo-2H-1-benzopyran-7-yl 4-methoxycarbonyloxybenzoate in 200 ml of ethanol. The reaction mixture is stirred for two hours, evaporated down and taken up in 100 ml diethyl ether. This solution is washed with water, dried, filtered to remove inorganic material and the filtrate evaporated down. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent and recrystallisation from acetonitrile to yield 9.5 g of 2-oxo-2H-1-benzopyran-7-yl 4-hydroxybenzoate.

Workup

  1. customevaporated down
  2. washThis solution is washed with water
  3. customdried
  4. filtrationfiltered
  5. customto remove inorganic material
  6. customthe filtrate evaporated down
  7. customThe residue is purified by column chromatography on silica gel
  8. customrecrystallisation from acetonitrile

Sources & evidence

ORD record
ord-99d7cfcd4db34573b14dfbcc349b24ea
Source dataset
uspto-grants-2004_02
Patent number
US06692797B1

Reaction notes

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