Potassium Nitrate → Benzyl 4-(chlorosulfonyl)butanoate

HRID 2271032Notes

Reaction equation

HRID 2271032 reaction equation
S[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[N+]([O-])([O-])=O.[K+].[S:20]([Cl:24])(Cl)(=[O:22])=[O:21].C([O-])(O)=O.[Na+]>>[Cl:24][S:20]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6])(=[O:22])=[O:21]

Participants

5

Reactant 4

HCID 24434Potassium NitrateHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 18387499Benzyl 4-mercaptobutyrate

Product 1

HCID 15377813Benzyl 4-(chlorosulfonyl)butanoateYield 75.1%

Procedure

To a mixture of benzyl 4-mercaptobutyrate (9.96 g, 47.4 mmol) and potassium nitrate (12 g, 118 mmol) was added dropwise sulfuryl chloride (16 g, 118 mmol) at 0° C., and the mixture was stirred for 10 hours at room temperature. The resulting suspension was adjusted to pH 7 with saturated NaHCO3 solution. The organic layer was separated, washed with saturated NaHCO3 solution and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was dissolved in CHCl3 and the solution was passed through short SiO2 column to give 9.85 g of benzyl 4-chlorosulfonylbutyrate as a slightly brown oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in CHCl3

Sources & evidence

ORD record
ord-a4b0961369984b61a2e0872a1ae9dba7
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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