Dimethyl Sulfate → Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetate

HRID 1018091Notes

Reaction equation

HRID 1018091 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=[O:6].[C:19](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:18])([CH3:17])[C:14]([O:16][CH3:19])=[O:15])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

Product 1

HCID 10062338Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetateYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Mix 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionic acid (10.0 g, 37.3 mmol) and anhydrous potassium carbonate (3.5 g, 25.3 mmol). Heat to 40° C. in acetonitrile (100 mL) and stir under a nitrogen atmosphere. Add dimethyl sulfate (13.3 g, 105 mmol) and reflux for 45 minutes. Evaporate the solvent in vacuo, dissolve the residue in ethyl acetate (50 mL) and wash with water (4×50 mL). Dry (MgSO4), filter through silica gel and evaporate the solvent in vacuo to give the title compound (6.4 g, 89%).

Workup

  1. customEvaporate the solvent in vacuo
  2. dissolutiondissolve the residue in ethyl acetate (50 mL)
  3. washwash with water (4×50 mL)
  4. dry with materialDry (MgSO4)
  5. filtrationfilter through silica gel
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-4903b18d644c46a5ace0db528ddb42d6
Source dataset
uspto-grants-2002_11
Patent number
US06479663B2

Reaction notes

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