Water → HCID 21182410, compound

HRID 1872381Notes

Reaction equation

HRID 1872381 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(OCC)(=O)C.O>N1C=CC=CC=1>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:6][CH2:5][CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 122964-Methyl-1-pentanol

Product 1

HCID 21182410HCID 21182410, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-methylpentanol (3.0 ml) in pyridine (20 ml) were added in turn with p-toluenesulfonyl chloride (4.6 g) and 4-N,N-dimethylaminopyridine (1.5 g) at ambient temperature. After stirring at ambient temperature, the reaction mixture was taken up into a mixture of ethyl acetate (100 ml) and water (100 ml). The separated organic layer was washed in turn with hydrochloric acid(1N), water, aqueous sodium hydrogencarbonate, and brine, and dried over magnesium sulfate. Evaporation gave 1-p-Toluenesulfonyloxy-4-methylpentane (5.30 g).

Workup

  1. washThe separated organic layer was washed in turn with hydrochloric acid(1N), water, aqueous sodium hydrogencarbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation

Sources & evidence

ORD record
ord-af822ff734f1453ebbd9c426ae6e14b0
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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