Water → HCID 89580837, compound

HRID 1501006Notes

Reaction equation

HRID 1501006 reaction equation
F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([CH3:15])[CH:3]=1.[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:15][C:4]1[CH:3]=[C:2]([O:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 895805714-Fluoro-2-methyl-benzoic acid tert-butyl ester

Product 1

HCID 89580837HCID 89580837, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of tert-butyl 4-fluoro-2-methylbenzoate (1 g, 4.8 mmol) in methylsulfinylmethane (45 mL) were added phenol (0.43 g, 4.6 mmol) and potassium carbonate (1.24 g, 9 mmol). Then the mixture was stirred at 130° C. for 12 hours. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL). The organic phase was separated, washed with water (20 mL). The organic phase was separated and concentrated to give a residue. The residue was purified by column chromatography (petroleum ether/ethyl acetate=10:1) to give tert-butyl 2-methyl-4-phenoxybenzoate (1.1 g, 86%) as a yellow solid. LRMS (M+H+) m/z: calcd 284.14. found 284.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. customThe organic phase was separated
  3. washwashed with water (20 mL)
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-7daf1a9f677f4196ba0ef5cd8048b3f3
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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