Water → Methyl 3-isopropoxybenzoate

HRID 369421Notes

Reaction equation

HRID 369421 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH:13]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 578499Methyl 3-isopropoxybenzoateYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 3-hydroxybenzoate (1 eq.) and 2-bromopropane (2 eq.) were dissolved in DMF. Subsequent to addition of potassium carbonate (2 eq.), the resulting mixture was stirred at 100° C. for 24 hours. The mixture was charged into water. Subsequent to extraction with ethyl acetate, the organic layer was washed with 1 N aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, whereby the title compound was obtained (yield: 49%).

Workup

  1. extractionSubsequent to extraction with ethyl acetate
  2. washthe organic layer was washed with 1 N aqueous solution of sodium hydroxide
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure, whereby the title compound
  5. customwas obtained (yield: 49%)

Sources & evidence

ORD record
ord-077c8fabeca64237936f6f26332f3fe2
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

Loading…