Diethyl Ether → 1-(4-Tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol

HRID 235718Notes

Reaction equation

HRID 235718 reaction equation
[CH2:1]([C:15]1[CH:26]=[CH:25][C:18]([O:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:27](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCOCC>N1C=CC=CC=1>[CH2:1]([C:15]1[CH:26]=[CH:25][C:18]([O:19][CH2:20][CH:21]([OH:24])[CH2:22][O:23][C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6456Trityl chlorideHCID 202198993-(4-Tetradecylphenoxy)-1,2-propanediol

Product 1

HCID 202184241-(4-Tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An about 364 mg portion of 3-(4-tetradecylphenoxy)-1,2-propanediol was dissolved in about 1.5 ml of dry pyridine and about 501 mg of tritylchloride was added. The mixture was stirred under argon for about 72 hours, ether was added and the mixture was washed with ice-cold dilute (about 1N) hydrochloric acid, sodium bicarbonate solution, brine, then dried and the solvent evaporated. The residue was recrystallized from ethanol, giving about 700 mg of the desired title compound.

Workup

  1. washthe mixture was washed with ice-cold
  2. additiondilute (about 1N) hydrochloric acid, sodium bicarbonate solution, brine
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-fe44f8932e254a7690164b70dac9d8df
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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