Sulfuryl chloride → [(Chlorocarbonyl)oxy]methyl acetate

HRID 915267Notes

Reaction equation

HRID 915267 reaction equation
[C:1](=[O:11])(SCC)[O:2][CH2:3][O:4][C:5](=[O:7])[CH3:6].S(Cl)([Cl:15])(=O)=O>>[C:1]([Cl:15])(=[O:11])[O:2][CH2:3][O:4][C:5](=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 14800954Carbonothioic acid, O-[(acetyloxy)methyl] S-ethyl ester

Product 1

HCID 14800978[(Chlorocarbonyl)oxy]methyl acetateYield 112.4%

Conditions

Temperature
0 °C

Procedure

To the thioester from Step 3 (2.50 g, 14.0 mmol) cooled to 0° C. is added sulfuryl chloride (1.5 mL, 18.25 mmol) over 2 min. The reaction mixture is stirred at 0° C. for 30 min then at RT for 2.5 h. The reaction mixture is concentrated and then dried on house vacuum overnight to afford 2.4 g of the desired crude product, which is used without further purification. 1H NMR (CDCl3) δ 5.83 (s, 2H), 2.19 (s, 3H);

Workup

  1. waitat RT for 2.5 h
  2. concentrationThe reaction mixture is concentrated
  3. customdried on house vacuum overnight

Sources & evidence

ORD record
ord-c02a1ee7a9f2455bbb03b104c2761006
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

Loading…