4-Toluenesulfonyl chloride → 16-(p-Toluensulfonyloxy)hexadecanol

HRID 366288

Reaction equation

HRID 366288 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>N1C=CC=CC=1>[C:25]1([CH3:26])[CH:27]=[CH:28][C:22]([S:19]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])(=[O:21])=[O:20])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 821841,16-Hexadecanediol

Product 1

HCID 1836647216-(p-Toluensulfonyloxy)hexadecanol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.1 g of 1,16-dihydroxyhexadecane in 10 ml of dry pyridine 0.8 g of tosyl chloride was added. After 2 h mixture was concentrated diluted with 20 ml of acetone, 5 g of SiO2 was added and acetone was removed in vacuum. The solid was applied on SiO2 and eluted with pentane-ethyl acetate (2:1) to yield 748 mg (42%) of C-101.

Workup

  1. concentrationAfter 2 h mixture was concentrated
  2. additiondiluted with 20 ml of acetone, 5 g of SiO2
  3. additionwas added
  4. customacetone was removed in vacuum
  5. washeluted with pentane-ethyl acetate (2:1)
  6. customto yield 748 mg (42%) of C-101

Sources & evidence

ORD record
ord-e13d3a98014543ba8b953bfdfb674d24
Source dataset
uspto-grants-2000_10
Patent number
US06130037

Linked notes

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