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

HRID 2051717Notes

Reaction equation

HRID 2051717 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([OH:9])=O.O=S(Cl)[Cl:12]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([Cl:12])=[O:9]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27642(2-Methoxyethoxy)acetic acid

Product 1

HCID 70103382-(2-Methoxyethoxy)acetyl chlorideYield 92.5%

Procedure

To 2-methoxyethoxyacetic acid (670 mg.; 4.00 mmoles) was added at 0°-2° under N2 atmosphere, SOCl2 (5ml.). 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 (νc=o, acid chloride).

Workup

  1. customExcess SOCl2 was evaporated
  2. additionthe residue was diluted with dry benzene (15 ml.)
  3. customevaporated again
  4. dry with materialdried over NaOH (in vacuo)

Sources & evidence

ORD record
ord-8f99db016fa2408abc29d612825814b7
Source dataset
uspto-grants-1980_01
Patent number
US04182711

Reaction notes

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