Dimethyl Sulfate → Methyl 6-methoxy-1-naphthoate

HRID 280484

Reaction equation

HRID 280484 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([OH:15])=[O:14])=[CH:8][CH:7]=[CH:6]2.[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 44137086-Methoxy-1-naphthoic acid

Product 1

HCID 10921906Methyl 6-methoxy-1-naphthoateYield 90.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 9.1 g of 6-methoxynaphthoic acid and 7.2 g of anhydrous potassium carbonate in 45 ml of acetone was heated to 50°-55° C. for 15 minutes, and 4.5 ml of dimethyl sulfate were then slowly dripped in over a period of 15 minutes. The mixture was then heated at reflux for one hour and cooled to room temperature, after which all the acetone was stripped under vacuum. After workup, it was determined that the process resulted in the formation of 8.85 g of methyl 6-methoxynaphthoate having an HPLC purity of 83.3%.

Workup

  1. temperaturewas heated to 50°-55° C. for 15 minutes
  2. customwere then slowly dripped in over a period of 15 minutes
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for one hour

Sources & evidence

ORD record
ord-cf08e29ea3514f6994e053f6eccc4c15
Source dataset
uspto-grants-1986_05
Patent number
US04590010

Linked notes

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