P-Cresol → Methyl (p-tolyloxy)acetate

HRID 2170624Notes

Reaction equation

HRID 2170624 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C>[C:3]1([CH3:8])[CH:4]=[CH:5][C:6]([O:7][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 10796Cesium carbonateHCID 60984Methyl bromoacetate

Product 1

HCID 601946Methyl (p-tolyloxy)acetateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of p-cresol (2 mL, 19.1 mmol) in anhydrous DMF (50 mL) were added Cs2CO3 (8.1 g, 24.9 mmol) and methyl bromoacetate (1.9 mL, 20.1 mmol). The suspension was stirred at room temperature for 3 h. After dilution with ethyl acetate, the reaction mixture was washed with a 0.5 N HCl solution, a saturated solution of NaHCO3, and brine, dried on MgSO4, and concentrated. The resulting oil was purified by chromatography on silica gel (Hexane/ethyl acetate 8/2) to afford the title compound as a colorless oil (3.10 g, 90%).

Workup

  1. washAfter dilution with ethyl acetate, the reaction mixture was washed with a 0.5 N HCl solution
  2. dry with materiala saturated solution of NaHCO3, and brine, dried on MgSO4
  3. concentrationconcentrated
  4. customThe resulting oil was purified by chromatography on silica gel (Hexane/ethyl acetate 8/2)

Sources & evidence

ORD record
ord-9ea61e8b2b854397a161c8d1f54b162f
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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