Dimethyl Sulfate → HCID 13554786, compound

HRID 256341Notes

Reaction equation

HRID 256341 reaction equation
[OH:1][C:2]1[C:3]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[CH:11][C:4]=2[O:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[C:19](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:19][O:1][C:2]1[C:3]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[CH:11][C:4]=2[O:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 86741843HCID 86741843, compound

Product 1

HCID 13554786HCID 13554786, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 25.0 g (0.10 mole) of 3-hydroxynaphtho [2,3-b]furan-2-carboxylic acid, methyl ester, 15.3 g (0.11 mole) of anhydrous potassium carbonate, and 10.6 ml (14.1 g, 11 mole of dimethyl sulfate in 500 ml of acetone is stirred at refux for 24 hours. The mixture is cooled, filtered, and the filter cake is washed several times with fresh acetone. The combined filtrates are evaporated (vacuum), and the residue is recrystallized from methanol to yield 20.3 g (77% yield) of the analytically pure 3-methoxynaphtho[2,3-b]furan-2-carboxylic acid, methyl ester, mp 121°-124 ° C.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. washthe filter cake is washed several times with fresh acetone
  4. customThe combined filtrates are evaporated (vacuum)
  5. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-d7f70b0c0b264bf89c5e92ca2d879520
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Reaction notes

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