Ethylene Glycol → 2-Trityloxyethanol

HRID 80298Notes

Reaction equation

HRID 80298 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]1([C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)Cl)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>N1C=CC=CC=1>[C:5]1([C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:3][CH2:2][CH2:1][OH:4])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 6456Trityl chloride

Product 1

HCID 3167932-TrityloxyethanolYield 24%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

Ethylene glycol (3.10 g, 49.9 mmol) (Wako Pure Chemical Industries, Ltd.) and triphenylchloromethane (1.39 g, 49.9 mmol) (Wako Pure Chemical Industries, Ltd.) were dissolved in pyridine (6 mL) (Wako Pure Chemical Industries, Ltd.), and the solution was heated to 45° C. and stirred for 2 hours. Water (50 mL) was poured into the reaction solution, and mixture was extracted with toluene (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with an hydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled of funder reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=9:1), to thereby obtain the title compound (0.37 g, 24% yield).

Workup

  1. extractionwas extracted with toluene (Wako Pure Chemical Industries, Ltd.)
  2. dry with materialThe organic layer was dried with an hydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  3. distillationthe solvent was distilled of funder reduced pressure

Sources & evidence

ORD record
ord-539387f15ac9479492f01f8763d5b64c
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

Loading…