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

HRID 2073897Notes

Reaction equation

HRID 2073897 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:8][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[O:7][CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 335O-CresolHCID 962WaterHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 10398141Ethyl 2-(2-methylphenoxy)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 10.8 g (0.1 mol) of o-cresol, 18.1 g (0.1 mol) of ethyl 2-bromopropionate, and 14.5 g of K2CO3 in 50 ml of DMF is heated at 70° C. for 3 days. The reaction mixture is poured into H2O, and extracted with ethyl acetate. The organic solution is dried and evaporated to give ethyl 2-(2-methylphenoxy)propionate which is used directly in the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic solution is dried
  3. customevaporated

Sources & evidence

ORD record
ord-f949238c31f447f9a52b0b061efe7b60
Source dataset
uspto-grants-1990_04
Patent number
US04920131

Reaction notes

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