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Hydrochloric Acid → 4-Chlorobutane-1-sulphonyl chloride

HRID 732428
Notes
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Reaction equation

HRID 732428 reaction equation
[S:1]([O-:4])([O-])=[O:2].[Na+].[Na+].C(O[CH2:11][CH2:12][CH2:13][CH2:14][Cl:15])(=O)C.[ClH:16]>O>[Cl:15][CH2:14][CH2:13][CH2:12][CH2:11][S:1]([Cl:16])(=[O:4])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 233991-Butanol, 4-chloro-, 1-acetateHCID 24437Sodium Sulfite

Product 1

HCID 742124-Chlorobutane-1-sulphonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add anhydrous sodium sulfite (16.8 g, 130 mmol) to a solution of 4-chlorobutyl acetate (20.0 g, 133 mmol) in water (50 mL) and reflux the mixture for 20 h. Cool to room temperature and add concentrated HCl (19.0 mL) and reflux for 1 h. Cool the mixture to room temperature, neutralize to about pH=7. Concentrate to about one half the volume, filter away the sodium chloride. Concentrate and dry to give the title compound.

Workup

  1. temperaturereflux the mixture for 20 h
  2. temperaturereflux for 1 h
  3. temperatureCool the mixture to room temperature
  4. concentrationConcentrate to about one half the volume
  5. filtrationfilter away the sodium chloride
  6. concentrationConcentrate
  7. customdry

Sources & evidence

ORD record
ord-d56b9ba0d8e84946ae969baed6e81415
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07585885B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes