Pyridine → 1-(2-Ethyl-4-tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol

HRID 34841Notes

Reaction equation

HRID 34841 reaction equation
[CH2:1]([C:3]1[CH:14]=[C:13]([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][CH3:28])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][OH:9])[CH3:2].[C:29](Cl)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:14]=[C:13]([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][CH3:28])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][O:9][C:29]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 142561973-(2-Ethyl-4-tetradecylphenoxy)-1,2-propanediol

Product 1

HCID 150302641-(2-Ethyl-4-tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanolYield 95.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 11.68 g of 3-(2-ethyl-4-tetradecylphenoxy)-1,2-propanediol, 14.95 g of trityl chloride and 40 ml pyridine was stirred for 72 hours, then diluted with chloroform, washed with two 100 ml portions of aqueous sodium bicarbonate, then water and dried. The solvents were evaporated under reduced pressure and the residue evaporated with toluene. This residue was then diluted with hexanes and the solid which formed collected giving 18 g of the desired compound.

Workup

  1. washwashed with two 100 ml portions of aqueous sodium bicarbonate
  2. dry with materialwater and dried
  3. customThe solvents were evaporated under reduced pressure
  4. customthe residue evaporated with toluene
  5. additionThis residue was then diluted with hexanes
  6. customthe solid which formed
  7. customcollected

Sources & evidence

ORD record
ord-3c43f253cc584c8da4fa19474bbfc3e5
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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