4-Toluenesulfonyl chloride → HCID 54214687, compound

HRID 1493866Notes

Reaction equation

HRID 1493866 reaction equation
[CH2:1]([O:8][CH:9]([CH2:12][O: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][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:10][OH:11])[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]>N1C=CC=CC=1>[CH2:1]([O:8][CH:9]([CH2:12][O: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][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:10][O:11][S:32]([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 131165252-(Benzyloxy)-3-(octadecyloxy)propan-1-OL

Product 1

HCID 54214687HCID 54214687, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 5 ml of pyridine were dissolved 1 g (2.3 mmole) of 2-O-benzyl-3-O-octadecylglycerol and 1.144 g (6.0 mmole) of tosyl chloride, and the solution was stirred at room temperature overnight. The reaction solution was concentrated to dryness under reduced pressure, and 20 ml of 10% aqueous hydrogencarbonate solution and 20 ml of ether were added to the residue, followed by shaking thoroughly. The ether layer was separated, dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was purified by 15 g of silica gel, with n-hexane-ethyl acetate (9:1) used as an eluent, to give 1.2 g (yield of 88.6%) of a colorless solid.

Workup

  1. concentrationThe reaction solution was concentrated to dryness under reduced pressure, and 20 ml of 10% aqueous hydrogencarbonate solution and 20 ml of ether
  2. additionwere added to the residue
  3. stirringby shaking thoroughly
  4. customThe ether layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by 15 g of silica gel, with n-hexane-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-b581a2b2b6444188a654a70147d38e58
Source dataset
uspto-grants-1991_06
Patent number
US05025005

Reaction notes

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