Acetone → HCID 18942446, compound

HRID 1272262Notes

Reaction equation

HRID 1272262 reaction equation
[OH:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2.[C:17](=O)([O-])[O-].[K+].[K+].CC(C)=O.COS(OC)(=O)=O>ClCCl.O>[OH:1][C:2]1[C:3]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH3:17])[CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium Carbonate2×HCID 11746080Methyl 3,5-dihydroxy-2-naphthoate

Product 1

HCID 18942446HCID 18942446, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 3,5-dihydroxy-2-naphthoate (3.27 g; 15 mmole) was mixed with potassium carbonate (3 g; 22 mmole), acetone (50 μL) was added and then dimethylsulfate (Merck) (1.56 mL; 16.5 mmole) was slowly added drop by drop. The reaction mixture was refluxed for 2 hours, cooled to room temperature and water (100 mL) was added thereto, whereat all potassium carbonate was dissolved. Dichloromethane (100 mL) was added to the solution and the layers were separated. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to dryness. The solid residue was recrystallized from methanol and 2.4 g (70%) of methyl 3-hydroxy-5-methoxy-2-naphthoate were obtained.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated to dryness
  6. customThe solid residue was recrystallized from methanol

Sources & evidence

ORD record
ord-d336be5604314f25bed49d0c46a637c7
Source dataset
uspto-grants-2007_04
Patent number
US07208518B2

Reaction notes

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