8-Methoxy-1,2-dihydro-benzo[f]chromen-3-one → 1,2-Dihydro-8-hydroxy-3H-naphtho[2,1-b]pyran-3-one

HRID 1648103Notes

Reaction equation

HRID 1648103 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13]1[CH2:12][CH2:11][C:10](=[O:17])[O:9][C:8]=1[CH:7]=[CH:6]2>C(O)C.C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13]1[CH2:12][CH2:11][C:10](=[O:17])[O:9][C:8]=1[CH:7]=[CH:6]2

Participants

3

Reactant 1

HCID 199219128-Methoxy-1,2-dihydro-benzo[f]chromen-3-one

Product 1

HCID 199219571,2-Dihydro-8-hydroxy-3H-naphtho[2,1-b]pyran-3-oneYield 70.3%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

Starting with 4.84 g (21.2 mmol) of 1,2-dihydro-8-methoxy-3H-naphtho[2,1-b]pyran-3-one from the preceding example, the title compound (3.19 g; 70.3%) was obtained as an off-white solid, mp 189°-199° C. (recrystallized from ethanol-ethyl acetate), using the procedure of example 221.

Sources & evidence

ORD record
ord-b3daf2a566634db9a17287ba61565e02
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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