Water → HCID 59498106, compound

HRID 2061026Notes

Reaction equation

HRID 2061026 reaction equation
[CH3:1][C:2](=[CH:7]OS(C1C=CC(C)=CC=1)(=O)=O)[C:3]([O:5][CH3:6])=[O:4].[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:7]/[C:2](=[CH:1]\[O:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)/[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 10796Cesium carbonateHCID 85441230HCID 85441230, compound

Product 1

HCID 59498106HCID 59498106, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.98 g (25.8 mmol) of methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate in 30 ml of DMF was added 2.67 g (28.3 mmol) of phenol and 10 g (30.6 mmol) of cesium carbonate and stirred at room temperature for 12 hours. The reaction solution was poured into water and extracted with tert-butyl methyl ether (twice). The combined organic layer was washed sequentially with a 1N aqueous NaOH solution, water, and a saturated NaCl solution, dried over anhydrous MgSO4, and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 657 mg of (E)-methyl 2-methyl-3-phenoxy-2-propenoate.

Workup

  1. extractionextracted with tert-butyl methyl ether (twice)
  2. washThe combined organic layer was washed sequentially with a 1N aqueous NaOH solution, water
  3. dry with materiala saturated NaCl solution, dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-64433e3af64942edac7db526bf2c7a7c
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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