Water → HCID 21182410, compound

HRID 1386598Notes

Reaction equation

HRID 1386598 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 (5.30g).

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-5fed4d0f5f3043bd970a90f05e9462b3
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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