Ethyl chloroacetate → HCID 68497911, compound

HRID 1176218Notes

Reaction equation

HRID 1176218 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:15][O:14][CH2:13][CH2:12][CH2:11][O:10][C:9]1[C:2]2[O:1][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:4][C:3]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 86609983HCID 86609983, compound

Product 1

HCID 68497911HCID 68497911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.95 g of 2-hydroxy-3-(3-methoxypropoxy)benzaldehyde, 1.16 ml of ethyl chloroacetate and 2.51 g of potassium carbonate in 100 ml of N,N-dimethylformamide is stirred at reflux over 19 hours. The reaction mixture is cooled, poured onto water (at 0° C.), stirred and subsequently extracted with dichloromethane (2×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.50 (1:1 EtOAc-heptane); Rt=4.72.

Workup

  1. temperatureat reflux over 19 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water (at 0° C.)
  4. stirringstirred
  5. extractionsubsequently extracted with dichloromethane (2×)
  6. dry with materialThe combined organic phases are dried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-27789682a98646198f72f21923266235
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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