O-Cresol → Ethyl 2-(2-methylphenoxy)propionate

HRID 585279Notes

Reaction equation

HRID 585279 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]1([CH3:14])[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C.C(OCC)C>[CH2:20]([O:19][C:17](=[O:18])[CH:16]([O:13][C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:14])[CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 335O-CresolHCID 10796Cesium carbonateHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 10398141Ethyl 2-(2-methylphenoxy)propionateYield 102.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Cesium carbonate (53.86 g, 165.3 mmol) was added to a solution of 2-cresol (10.0 g, 92.5 mmol) in anhydrous DMF (500 mL) at room temperature under an atmosphere of nitrogen. After five minutes, ethyl 2-bromopropionate (16.7 mL, 92.5 mmol, d=1.394) was added rapidly dropwise and the resultant mixture was allowed to stir at 90° C. for 18 h. The reaction mixture was diluted with diethyl ether, then extracted twice with 1N HCl and twice with water. The organic layer was dried over MgSO4 and concentrated in vacuo to provide the title compound (19.7 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.16 (d, 1H, J=7.43 Hz), 7.11 (t, 1H, J=7.43 Hz), 6.89 (t, 1H, J=7.48 Hz), 6.70 (d, 1H, J=7.43 Hz), 4.75 (q, 1H, J=6.65 Hz), 4.23 (q, 2H, J=6.65 Hz), 2.30 (s, 3H), 1.64 (dd, 3H, J=7.04 Hz, 0.78 Hz), 1.26 (td, 3H, J=7.04 Hz, 0.78 Hz). Rf=0.37 in 25% ether in hexanes.

Workup

  1. extractionextracted twice with 1N HCl and twice with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-781f780291614758a436ec446f3f9ada
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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