Sulfuryl chloride → [(Chlorocarbonyl)oxy]methyl 2-methylpropanoate

HRID 843092Notes

Reaction equation

HRID 843092 reaction equation
C(S[C:4]([O:6][CH2:7][O:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])=[O:5])C.S(Cl)([Cl:17])(=O)=O>>[Cl:17][C:4]([O:6][CH2:7][O:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])=[O:5]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 85885666Isobutyric acid ethylsulfanylcarbonyloxymethyl ester

Product 1

HCID 19067202[(Chlorocarbonyl)oxy]methyl 2-methylpropanoate

Conditions

Temperature
-40 °C

Procedure

A 100 mL roundbottom flask was charged with the 2-methylpropanoic acid ethylsulfanylcarbonyloxymethyl ester (2.91 g, 14.1 mmol) and cooled to −40° C. in an acetone dry ice bath. Sulfuryl chloride (1.90 g, 14.1 mmol) was added over one minute. After 10 minutes the acetone/dry ice cooling bath was removed and replaced with an ice/water bath. After 30 minutes of stirring, the cooling bath was removed and the reaction was allowed to stir for one hour at room temperature and then placed under vacuum for 90 minutes. The material was used without purification. 1H-NMR (300 MHz, CDCl3) δ (ppm): 1.22 (d, 6H), 2.65 (m, 1H), 5.83 (s, 2H).

Workup

  1. customAfter 10 minutes the acetone/dry ice cooling bath was removed
  2. customreplaced with an ice/water bath
  3. customthe cooling bath was removed
  4. stirringto stir for one hour at room temperature
  5. waitplaced under vacuum for 90 minutes
  6. customThe material was used without purification

Sources & evidence

ORD record
ord-b73f26dc820f47d092217a32031e4425
Source dataset
uspto-grants-2002_04
Patent number
US06376548B1

Reaction notes

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