Methanol → 9H-Xanthen-9-one, 3-methoxy-

HRID 1275527Notes

Reaction equation

HRID 1275527 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O-:16].[Na+].C[OH:19].O>CCO>[CH3:15][O:16][C:5]1[CH:4]=[CH:3][C:2]2[C:1](=[O:8])[C:9]3[C:14]([O:19][C:7]=2[CH:6]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3102BenzophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 773099H-Xanthen-9-one, 3-methoxy-Yield 80.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the benzophenone intermediate (12.51 g) in EtOH (200 ml) was treated with a solution of NaOMe in MeOH (25 wt. %, 22.86 ml, 0.1 mole) at room temperature, the color of the mixture changed from yellow to orange immediately. The reaction mixture was brought to reflux for 100 min. Cooled to 0°, the reaction mixture was treated with water (100 ml), to produce a fine white precipitate. The solid was filtered on a Buchner funnel, washed with water and EtOH, and finally dried in vacuo, yielding 3-methoxy-9H-xanthen-9-one 8 (9.12 g, 80.7%) as a white powder: m.p. 127-129° C.; 1H NMR (CDCl3): delta 8.31 (1H, dd, J=7.9, 1.2 Hz), 8.23 (1H, J=8.6 Hz), 7.68 (1H, m), 7.44 (1H, d, J=8.6 Hz), 7.35 (1H, m), 6.93 (1H, m), 6.87 (1H, d, J=2.4 Hz) and 3.92 (3H, s); 1R (CHCl3): 2999, 1644, 1605, 1460, 1434, 1321, 1273, 1254, 1159, 1101, 1029, 968 and 848 cm-1.

Workup

  1. temperatureto reflux for 100 min
  2. temperatureCooled to 0°
  3. customto produce a fine white precipitate
  4. filtrationThe solid was filtered on a Buchner funnel
  5. washwashed with water and EtOH
  6. customfinally dried in vacuo

Sources & evidence

ORD record
ord-86de36b9ce664fa5b9b5fa680bfe062a
Source dataset
uspto-grants-2000_12
Patent number
US06162610

Reaction notes

Loading…