Hydrogen Bromide → 4,6-Dihydroxy-3-phenyl-coumarin

HRID 904304Notes

Reaction equation

HRID 904304 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8](=[O:13])[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:6]2[OH:20].Br.C(OC(=O)C)(=O)C.O1CCOCC1.C(OC(C)C)(C)C>C(O)(=O)C>[OH:20][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([OH:2])[CH:4]=2)[O:9][C:8](=[O:13])[C:7]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 7918Acetic AnhydrideHCID 547058964-Hydroxy-6-methoxy-3-phenyl-2H-1-benzopyran-2-oneHCID 67198123Dioxane diisopropyl ether

Product 1

HCID 547213354,6-Dihydroxy-3-phenyl-coumarinYield 33.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared in the manner described in Example 25, Stage A, from 37.6 g. (0.14 mol) of 6-methoxy-4-hydroxy-3-phenyl-coumarin, 375 ml. of glacial acetic acid, 750 ml. of 62% hydrobromic acid and 375 ml. of acetic anhydride. Weight 12.2 g.; yield 33.7% (theoretical yield 35.6 g.); M.P. 261°-263° C. (dioxane-diisopropyl ether: 50-50).

Workup

  1. customPrepared in the manner

Sources & evidence

ORD record
ord-76a01896133b4ab4885dc3f97abfa7bd
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

Loading…