Methanol → (3-Bromo-6-hydroxy-2-methylphenyl)(2,3,4-trimethoxy-6-methylphenyl)methanone

HRID 365962Notes

Reaction equation

HRID 365962 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:24]C(=O)C(C)(C)C)=[C:6]([C:22]=1[CH3:23])[C:7]([C:9]1[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[C:10]=1[O:20][CH3:21])=[O:8].C(=O)([O-])[O-].[Na+].[Na+].CO>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C:22]=1[CH3:23])[C:7]([C:9]1[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[C:10]=1[O:20][CH3:21])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 226713735-Bromo-6,6'-dimethyl-2-pivaloyloxy-2',3',4'-trimethoxybenzophenone

Product 1

HCID 10938097(3-Bromo-6-hydroxy-2-methylphenyl)(2,3,4-trimethoxy-6-methylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 50B (5.1 g, 10.6 mmol), sodium carbonate (3.65 g), methanol (100 ml) and water (30 ml) is heated to reflux with stirring for 1 hour. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic phase is separated and concentrated. The residue is recrystallized from petrol ethers/ethyl acetate (95:5 v/v) The pure product is obtained as yellowish crystals, 3.70 g (88.3%), mp. 119-120° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is separated
  5. concentrationconcentrated
  6. customThe residue is recrystallized from petrol ethers/ethyl acetate (95:5 v/v) The pure product
  7. customis obtained as yellowish crystals, 3.70 g (88.3%), mp. 119-120° C.

Sources & evidence

ORD record
ord-f02ea5dae1e74f5a99b1f54c696dcb66
Source dataset
uspto-grants-2000_10
Patent number
US06127570

Reaction notes

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