Ethyl chloroacetate → Ethyl 2-(3-methoxyphenoxy)acetate

HRID 1804784Notes

Reaction equation

HRID 1804784 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH2:10]([O:12][C:13](=[O:16])[CH2:14]Cl)[CH3:11].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:10]([O:12][C:13](=[O:16])[CH2:14][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:11]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 90073-MethoxyphenolHCID 11430Potassium Carbonate

Product 1

HCID 21506379Ethyl 2-(3-methoxyphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

3-Methoxy-phenol (43.4 ml, 400 mmol) is dissolved in acetone (800 ml) and after addition of chloro-acetic acid ethyl ester (42.6 ml, 400 mmol) and K2CO3 (111 g, 800 mmol) the mixture is refluxed for 22 h. After cooling down to 0° C., the mixture is filtrated and the filtrate is evaporated under reduced pressure. The residue is diluted in ethyl acetate, cooled to 0° C. and washed with aqueous NaOH solution. The organic layer is dried over sodium sulfate and evaporated under reduced pressure.

Workup

  1. temperatureis refluxed for 22 h
  2. filtrationthe mixture is filtrated
  3. customthe filtrate is evaporated under reduced pressure
  4. additionThe residue is diluted in ethyl acetate
  5. temperaturecooled to 0° C.
  6. washwashed with aqueous NaOH solution
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-51f606d788c94813a071beb6a7e7e59d
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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