1-Butanol → 6,6'-Dimethyl-2'-n-butoxy-2,3',4'-trimethoxy-benzophenone

HRID 1586580Notes

Reaction equation

HRID 1586580 reaction equation
[CH2:1](O)[CH2:2][CH2:3]C.[H-].[Na+].[CH3:8][C:9]1[C:14]([C:15]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([O:24][CH3:25])=[C:19]([O:26][CH3:27])[C:18]=2[O:28][CH3:29])=[O:16])=[C:13]([O:30][CH3:31])[CH:12]=[CH:11][CH:10]=1.C(COC)OC>C(OCC)(=O)C.O>[CH3:8][C:9]1[C:14]([C:15]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([O:24][CH3:25])=[C:19]([O:26][CH3:27])[C:18]=2[O:28][CH2:29][CH2:1][CH2:2][CH3:3])=[O:16])=[C:13]([O:30][CH3:31])[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 154310606,6'-Dimethyl-2,2',3',4'-tetramethoxy-benzophenone

Product 1

HCID 158708956,6'-Dimethyl-2'-n-butoxy-2,3',4'-trimethoxy-benzophenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of n-butanol (5 ml) and sodium hydride (60% in oil, 10 mmol) is stirred until the formation of H2 gas ceases. A mixture of 1C (0.7 g, 2,2 mmol) and dimethoxyethane (15 ml) is added to the resulting reaction mixture. Subsequently, the reaction mixture is heated under reflux with stirring for 24 hours. A mixture of water and ethyl acetate (1:1 v/v; 100 ml) is then slowly added at room temperature. The organic phase is separated, concentrated and the residue is purified by column chromatography (petrol ether:ethyl acetate, 95:5 v/v) yielding the pure product as a yellow oil, 0.2 g, (24.4%).

Workup

  1. additionis added to the resulting reaction mixture
  2. temperatureSubsequently, the reaction mixture is heated
  3. temperatureunder reflux
  4. stirringwith stirring for 24 hours
  5. additionis then slowly added at room temperature
  6. customThe organic phase is separated
  7. concentrationconcentrated
  8. customthe residue is purified by column chromatography (petrol ether:ethyl acetate, 95:5 v/v)

Sources & evidence

ORD record
ord-11135ef9fb5a43a49afc104af9193e1b
Source dataset
uspto-grants-1999_08
Patent number
US05945567

Reaction notes

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