4-Toluenesulfonyl chloride → HCID 54214687, compound

HRID 649052Notes

Reaction equation

HRID 649052 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 hydrogen-carbonate 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 hydrogen-carbonate 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-9f09a93b8e6b4f7ca1d382fd81edcca0
Source dataset
uspto-grants-1988_04
Patent number
US04737518

Reaction notes

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