4-Toluenesulfonyl chloride → HCID 57583239, compound

HRID 1645498Notes

Reaction equation

HRID 1645498 reaction equation
[OH:1][CH2:2][CH:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:4][CH2:5][OH:6].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[S:17]([O:6][CH2:5][CH2:4][CH:3]([CH2:2][O:1][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18])[CH2:7][CH2:8][CH2:9][O:10][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18])([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10898853HCID 10898853, compound

Product 1

HCID 57583239HCID 57583239, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-hydroxymethylhexane-1,6-diol (4 g, 0.027 mol) in pyridine (80 mL) stirred in an ice bath was added para-toluenesulphonyl chloride (16.9 g, 0.09 mol) in one portion. The mixture was allowed to warm to ambient temperature. After 48 hours the reaction was worked up using DCM (100 mL) which was washed with 1N HCl (2×100 mL). The organic layer was dried and concentrated to yield a very viscous, sticky oil which was analysed by NMR. This confirmed the desired material had been formed in a yield of 60% (9.9 g). The material was used without further purification.

Workup

  1. washDCM (100 mL) which was washed with 1N HCl (2×100 mL)
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto yield a very viscous, sticky oil which
  5. customhad been formed in a yield of 60% (9.9 g)
  6. customThe material was used without further purification

Sources & evidence

ORD record
ord-02eff92c761044f4921caafc2166c6c2
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

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