Dimethyl Sulfate → 2-(4-Fluoro-phenoxy)-6-methyl-benzoic acid methyl ester

HRID 706180Notes

Reaction equation

HRID 706180 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:19]OS(OC)(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(C(CC)=O)C>[CH3:19][O:10][C:9](=[O:11])[C:8]1[C:12]([CH3:16])=[CH:13][CH:14]=[CH:15][C:7]=1[O:6][C:5]1[CH:17]=[CH:18][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 671102182-(4-Fluoro-phenoxy)-6-methyl-benzoic acid

Product 1

HCID 671101342-(4-Fluoro-phenoxy)-6-methyl-benzoic acid methyl esterYield 97.8%

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Procedure

A mixture of 2-(4-fluoro-phenoxy)-6-methyl-benzoic acid (21.6 mmol, 5.32 g), dimethylsulfate (43.2 mmol, 4.2 mL), K2CO3 (43.2 mmol, 6 g), and diethyl ketone (80 mL) was refluxed with stirring for 18 h before it was concentrated in vacuo. To the residue was added water (50 mL) and the mixture was extracted with ethyl acetate (1×100 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a tan oil (5.5 g); 1H NMR (CDCl3, 200 MHz): δ=7.20 (t, 1H), 6.92 to 7.04 (m, 5H), 6.66 (d, 1H), 3.84 (s, 3H), 2.35 (s, 3H).

Workup

  1. temperaturewas refluxed
  2. concentrationwas concentrated in vacuo
  3. additionTo the residue was added water (50 mL)
  4. extractionthe mixture was extracted with ethyl acetate (1×100 mL)
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3cf6351589e045f78dc8fdd1e71364dc
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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