Chloroacetic Acid → [2-(2-Methoxyphenyl)ethoxy]acetic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][OH:11].[H-].[Na+].Cl[CH2:15][C:16]([OH:18])=[O:17]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][O:11][CH2:15][C:16]([OH:18])=[O:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
The solution of 10.0 g of 2-(2-methoxyphenyl)ethanol in 130 ml of dimethyl sulphoxide is admixed with stirring with sodium hydride dispersion (60%) and stirred at 60° C. over 10 min. The suspension is admixed slowly with 6.20 g of chloroacetic acid and subsequently stirred at 80° C. over 2 hours. The reaction mixture is cooled, poured onto ice-water (0.5 l) and washed with ethyl acetate (1×250 ml). The aqueous phase is acidified with 2M HCl and extracted with ethyl acetate (2×250 ml). The organic phases are washed successively with water (250 ml) and brine (1×250 ml), dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.04 (200:20:1 dichloromethane-methanol-conc. ammonia); Rt=3.44.
Workup
- stirringsubsequently stirred at 80° C. over 2 hours
- temperatureThe reaction mixture is cooled
- additionpoured onto ice-water (0.5 l)
- washwashed with ethyl acetate (1×250 ml)
- extractionextracted with ethyl acetate (2×250 ml)
- washThe organic phases are washed successively with water (250 ml) and brine (1×250 ml)
- dry with materialdried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4fdc2a4eb04147769a9bca4873110804
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790715B2
Reaction notes
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