4-Toluenesulfonyl chloride → HCID 21849470, compound

HRID 1451579Notes

Reaction equation

HRID 1451579 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1>[C:24]1([CH3:25])[CH:26]=[CH:27][C:21]([S:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:12][CH:11]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10681222HCID 10681222, compound

Product 1

HCID 21849470HCID 21849470, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(4-Hexylphenyl)butanol (5.0 g) was dissolved in 20 ml of pyridine and 4.88 g of tosyl chloride was added thereto. The reaction mixture was left standing at room temperature overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with 2N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and saturated brine in order and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:7) to give 2.21 g of 4-(4-hexylphenyl)butyl p-toluenesulfonate as a colorless, oily substance.

Workup

  1. waitThe reaction mixture was left
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 2N hydrochloric acid
  4. concentrationa saturated aqueous sodium bicarbonate solution and saturated brine in order and concentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:7)

Sources & evidence

ORD record
ord-493872e9159945628d72ffbfe20d49df
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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