4-Toluenesulfonyl chloride → 1-(2-Benzyloxy-3-octadecyloxy)propyl tosylate

HRID 649051Notes

Reaction equation

HRID 649051 reaction equation
[CH2:1]([O:8][CH:9]([CH:11]([O:27][CH:28]([OH:31])[CH2:29][CH3:30])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:32](Cl)([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33]>C(N(CC)CC)C>[S:32]([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)([O:31][CH:28]([O:27][CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:10])[CH2:29][CH3:30])(=[O:34])=[O:33]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 54196752HCID 54196752, compound

Product 1

HCID 198292711-(2-Benzyloxy-3-octadecyloxy)propyl tosylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
65 °C

Procedure

In 24 ml of triethylamine were dissolved 1.3 g (3 mmole) of 1-(2-benzyloxy-3-octadecyloxy)propanol and 1.7 g (9 mmole) of tosyl chloride, and the solution was warmed at 65° C. and stirred for 1.5 days. The reaction solution was concentrated to dryness under reduced pressure, and the residue was dissolved in chloroform. The solution was washed with water, dried over potassium carbonate. The solvent was distilled off under reduced pressure, and the residue was subjected to separation and purification by chromatography on a column of 40 g of silica gel. From the eluate of n-hexane-ethyl acetate (4:1), there was obtained the objective compound in the form of a colorless oil. Yield of 1.4 g (83%).

Workup

  1. concentrationThe reaction solution was concentrated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with water
  4. dry with materialdried over potassium carbonate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was subjected to separation and purification by chromatography on a column of 40 g of silica gel
  7. customFrom the eluate of n-hexane-ethyl acetate (4:1), there was obtained the objective compound in the form of a colorless oil

Sources & evidence

ORD record
ord-4e17e5a098094300ba960992d1906ef8
Source dataset
uspto-grants-1988_04
Patent number
US04737518

Reaction notes

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