Diethyl Ether → 3-O-Octadecyl-2-O-tosyl-1-O-tritylglycerol

HRID 442703Notes

Reaction equation

HRID 442703 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:22])[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][CH3:18].[C:44]1([CH3:54])[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=1.C(OCC)C>O>[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:22][S:50]([C:47]1[CH:48]=[CH:49][C:44]([CH3:54])=[CH:45][CH:46]=1)(=[O:52])=[O:51])[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][CH3:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

Product 1

HCID 135065293-O-Octadecyl-2-O-tosyl-1-O-tritylglycerol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
4 °C

Procedure

A solution of 1-O-octadecyl-3-O-tritylglycerol (173.51 g, 295.63 mmol) in 895 mL water free pyridine is added to a solution of p-toluenesulfonyl chloride (88.49 g, 464.15 mmol) in 670 mL water-free pyridine with constant stirring. The reaction mixture is kept at ambient temperature (20°-23° C.) for two days. Diethyl ether (2.8 L) is added to this reaction mixture and the organic phase is washed six times with water, twice with diluted aqueous sodium carbonate, and then washed with water until neutral. After drying the organic phase over sodium sulfate, the solvent is removed under reduced pressure. The residue is triturated with isopropanol (1140 mL) with stirring until the product crystallizes. After cooling to 4° C., the product, 1-O-octadecyl-2-O-p-toluenesulfonyl-3-O-tritylglycerol, is isolated by filtration, washed with isopropanol and dried under vacuum.

Workup

  1. customis kept at ambient temperature
  2. custom(20°-23° C.)
  3. customfor two days
  4. washthe organic phase is washed six times with water
  5. washtwice with diluted aqueous sodium carbonate, and then washed with water until neutral
  6. dry with materialAfter drying the organic phase over sodium sulfate
  7. customthe solvent is removed under reduced pressure
  8. customThe residue is triturated with isopropanol (1140 mL)
  9. customcrystallizes

Sources & evidence

ORD record
ord-39bf514afbac449c962f4c9b7e1a9336
Source dataset
uspto-grants-1999_04
Patent number
US05891881

Reaction notes

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