Sulfuric Acid → 1-(4-Bromophenyl)-3,3-dimethoxy propan-1-one

HRID 334451Notes

Reaction equation

HRID 334451 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=[O:3].[CH:11]([O:13][CH3:14])=[O:12].C[O-].[Na+].S(O[CH3:23])(O)(=O)=O.S(=O)(=O)(O)O.[OH-].[Na+]>O.C(OCC)(=O)C.CO.O1CCCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][CH:11]([O:12][CH3:23])[O:13][CH3:14])=[CH:5][CH:6]=1

Participants

11

Reactant 6

HCID 1118Sulfuric Acid3×HCID 6412Monomethyl sulfateHCID 7466p-BromoacetophenoneHCID 7865Methyl formateHCID 14798Sodium HydroxideHCID 10942334Sodium Methoxide

Product 1

HCID 665988111-(4-Bromophenyl)-3,3-dimethoxy propan-1-one

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran (206 mL) solution of 4-bromoacetophenone (61.4 g) and methyl formate (27.8 g) was added dropwise to a tetrahydrofuran (125 mL) suspension of sodium methoxide (25 g) under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added dropwise to a methanol sulfate solution (prepared by adding sulfuric acid (45.4 g) dropwise to methanol (150 mL) under ice cooling) at room temperature, and the mixture was stirred for 2 days. The reaction mixture was added dropwise at −5° C. to a 1 mol/L aqueous sodium hydroxide solution (925 mL), and then a 5 mol/L sulfuric acid aqueous solution was added thereto at the same temperature until the pH was 8. After ethyl acetate (500 mL) and water (500 mL) were added thereto, a 5 mol/L sulfuric acid aqueous solution was added at −5° C. until the pH was 8. The organic layer was separated and the water layer was extracted with ethyl acetate. Together with the organic layer, the water layer was sequentially washed with a 1 mol/L sodium chloride solution and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure, thereby giving 80 g of a target compound as an oily product.

Workup

  1. customprepared
  2. stirringthe mixture was stirred for 2 days
  3. customThe organic layer was separated
  4. extractionthe water layer was extracted with ethyl acetate
  5. washTogether with the organic layer, the water layer was sequentially washed with a 1 mol/L sodium chloride solution
  6. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7f8470e02ae463ead3f54eefb3b7998
Source dataset
uspto-grants-2014_11
Patent number
US08883824B2

Reaction notes

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