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

HRID 703321Notes

Reaction equation

HRID 703321 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

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 8028TetrahydrofuranSolvent

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-8761bd02f07c47828a0b483a3266b0fe
Source dataset
uspto-grants-1991_01
Patent number
US04981989

Reaction notes

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