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p-(Chlorodiphenylmethyl)anisole → 1-[(4-Methoxyphenyl)diphenylmethoxy]-3-(3-tetradecylphenoxy)-2-propanol

HRID 329975
Notes
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Reaction equation

HRID 329975 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[CH2:23]([C:37]1[CH:38]=[C:39]([CH:46]=[CH:47][CH:48]=1)[O:40][CH2:41][CH:42]([OH:45])[CH2:43][OH:44])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>O1CCCC1.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:44][CH2:43][CH:42]([OH:45])[CH2:41][O:40][C:39]2[CH:46]=[CH:47][CH:48]=[C:37]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:38]=2)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 84462p-(Chlorodiphenylmethyl)anisoleHCID 148196583-(3-Tetradecylphenoxy)-1,2-propanediol

Product 1

HCID 148196591-[(4-Methoxyphenyl)diphenylmethoxy]-3-(3-tetradecylphenoxy)-2-propanolYield 89.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028Tetrahydrofuran
Solvent

Procedure

A solution of 25.94 g of 4-methoxytrityl chloride in 15 ml of dry tetrahydrofuran was added to a stirred solution of 21.84 g of 3-(3-tetradecylphenoxy)-1,2-propanediol in 40 ml of pyridine under argon. This mixture was stirred overnight, the solvents removed under reduced pressure and the residue dissolved in chloroform. This solution was washed with saturated aqueous sodium bicarbonate, then water, dried and evaporated, giving 34.3 g of the desired compound.

Workup

  1. customthe solvents removed under reduced pressure
  2. dissolutionthe residue dissolved in chloroform
  3. washThis solution was washed with saturated aqueous sodium bicarbonate
  4. dry with materialwater, dried
  5. customevaporated

Sources & evidence

ORD record
ord-a5e5bba0d97f4f32881cae73de16acd9
Source dataset
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04894367

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes