Thionyl Chloride → 2-(2-Methoxyethoxy)acetyl chloride

Participants

Reaction Steps

To 2-methoxyethoxyacetic acid (670 mg.; 4.00 mmoles) was added at 0°-2° under N2 atmosphere, SOCl2 (5 ml.). The mixture was stirred at room temperature under N2 for 2 hours. Excess SOCl2 was evaporated and the residue was diluted with dry benzene (15 ml.), evaporated again, and dried over NaOH (in vacuo) to yield 2-methoxyethoxyacetyl chloride (705 mg.; 4.62 mmoles; yield 92.5%) as a colorless liquid. nmr (CDCl3): δppm 3.40 (3H, s, --OCH3), 3.4-3.9 (4H, m, --CH2CH2 --), 4.56 (2H, s, ClOCH2O--); ir (neat): 1810 cm-1 (γc=o, acid chloride).

Provenance & Evidence