Dimethyl Sulfate → HCID 12535017, compound

HRID 638108

Reaction equation

HRID 638108 reaction equation
[C:1]1([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.S(OC)(O[CH3:20])(=O)=O.[Cl-].[NH4+]>S(C1C=CC(C)=CC=1)([O-])(=O)=O.C([N+](CC)(CC)CC)C.C(#N)C.[Pt]>[C:1]1([CH:11]([CH3:20])[C:12]([O:14][CH3:15])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 17891Methyl 1-naphthylacetate2×HCID 25517Ammonium Chloride

Product 1

HCID 12535017HCID 12535017, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 101846Tetraethylammonium p-toluenesulphonateCatalyst2×HCID 6342AcetonitrileSolvent2×

Procedure

Into the cathode chamber of an electrolytic cell divided with an ion-exchange resin diaphragm was placed a solution of 10 mmols of methyl 1-naphthylacetate, 12 mmols of dimethyl sulfate and 1.0 g of tetraethylammonium tosylate in 30 ml of acetonitrile. The anode chamber was supplied with a solution of 2.0 g of tetraethylammonium tosylate in 10 ml of acetonitrile. Constant current electrolysis was conducted at 0.2 A/cm2 with use of platinum for both the cathode and the anode. After passing 1.5 F of electricity per mol of the methyl 1-naphthylacetate at room temperature, the cathode solution was added to a saturated aqueous solution of ammonium chloride and the mixture was extracted twice with ether. The ether was distilled off and the residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1), giving methyl 1-naphthyl(α-methyl)acetate in a yield of 92%. The spectral data of the ester were as follows.

Workup

  1. customat room temperature
  2. extractionthe mixture was extracted twice with ether
  3. distillationThe ether was distilled off
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-70deb93fc4804ea488aee74faaaa8c33
Source dataset
uspto-grants-1985_12
Patent number
US04560447

Linked notes

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