Sulfuric Acid → 3,3,3-Trinitropropyl Pentafluorothioacetate

HRID 231915

Reaction equation

HRID 231915 reaction equation
[F:1][S:2]([F:9])=[C:3]([OH:8])[C:4]([F:7])([F:6])[F:5].[N+:10]([C:13]([N+:20]([O-:22])=[O:21])([N+:17]([O-:19])=[O:18])[CH2:14][CH2:15]O)([O-:12])=[O:11].S(=O)(=O)(O)O>ClCCCl>[F:1][S:2]([F:9])=[C:3]([O:8][CH2:15][CH2:14][C:13]([N+:17]([O-:19])=[O:18])([N+:10]([O-:12])=[O:11])[N+:20]([O-:22])=[O:21])[C:4]([F:7])([F:6])[F:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 130864113,3,3-Trinitropropan-1-olHCID 86743239Pentafluorothioacetic acid

Product 1

HCID 571744253,3,3-Trinitropropyl PentafluorothioacetateYield 95.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 0.57 g (0.003 mole) of pentafluorothioacetic acid, 1.2 g (0.006 mole) of 3,3,3-trinitropropanol and 0.3 ml of concentrated sulfuric acid in 10 ml of 1,2-dichloroethane was stirred at reflux temperature for 24 hr in a flask with a reverse Dean Stark trap attached. The reaction mixture was cooled and the organic layer was decanted from the insoluble sulfuric acid. After the removal of volatiles from the organic layer, the residue (oil) was chromatographed on silica gel 40 using methylene chloride as eluent to give 0.99 g (89%) of product, mp 32° C.;

Workup

  1. temperatureat reflux temperature for 24 hr in a flask with a reverse Dean Stark trap
  2. temperatureThe reaction mixture was cooled
  3. customthe organic layer was decanted from the insoluble sulfuric acid
  4. customAfter the removal of volatiles from the organic layer
  5. customthe residue (oil) was chromatographed on silica gel 40 using methylene chloride as eluent

Sources & evidence

ORD record
ord-abdf7bfce7b04fe9a4f601d7cb38d772
Source dataset
uspto-grants-1989_07
Patent number
US04849540

Linked notes

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