1,2-Dimethoxyethane → 3,4,8-Trimethoxy-1-methylxanthen-9-one

HRID 1368809Notes

Reaction equation

HRID 1368809 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[C:3]=1[C:9]([C:11]1[C:16]([CH3:17])=[CH:15][C:14]([O:18][CH3:19])=[C:13]([O:20][CH3:21])[C:12]=1[OH:22])=[O:10].[Na].[CH2:24](COC)[O:25]C>CO>[CH3:19][O:18][C:14]1[CH:15]=[C:16]([CH3:17])[C:11]2[C:9](=[O:10])[C:3]3[C:4]([O:22][C:12]=2[C:13]=1[O:20][CH3:21])=[CH:5][CH:6]=[CH:7][C:2]=3[O:25][CH3:24]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 5360545SodiumHCID 185173952,6-Dichloro-3',4'-dimethoxy-2'-hydroxy-6'-methylbenzophenone

Product 1

HCID 185173933,4,8-Trimethoxy-1-methylxanthen-9-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

At about 0-5° C. under a protective atmosphere, 37.5 g (0.11 mol) of the benzophenone derivative from Example 1a in 100 ml of dimethoxyethane were added to a solution of 2.6 g (110 mol) of sodium in 50 ml of methanol. After about 72 hours of stirring at 80° C., the title compound was precipitated by adding a 1:1 mixture of water and ethyl acetate. 33.4 g (100% of theory) of product of m.p. 158° C. were isolated by filtration.

Workup

  1. customthe title compound was precipitated
  2. additionby adding
  3. additiona 1:1 mixture of water and ethyl acetate
  4. custom33.4 g (100% of theory) of product of m.p. 158° C. were isolated by filtration

Sources & evidence

ORD record
ord-72e3998bb34d46f4b43b36c9140eebc0
Source dataset
uspto-grants-2003_06
Patent number
US06576595B1

Reaction notes

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