Hydrochloric Acid → 3-(Hexadecyloxy)-1-(triphenylmethoxy)-2-butanol

HRID 1761731Notes

Reaction equation

HRID 1761731 reaction equation
[CH2:1]([O:17][CH:18]([CH3:23])[CH:19]([OH:22])[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:24](Cl)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N1C=CC=CC=1.Cl>O>[CH2:1]([O:17][CH:18]([CH3:23])[CH:19]([OH:22])[CH2:20][O:21][C:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=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][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6456Trityl chlorideHCID 142331613-Hexadecyloxybutane-1,2-diol

Product 1

HCID 142331663-(Hexadecyloxy)-1-(triphenylmethoxy)-2-butanolYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 27.5 g of 3-(hexadecyloxy)-1,2-butanediol, 34.79 g of trityl chloride and 125 ml of pyridine was allowed to stand 48 hours and then poured into water. A mixture of ether-petroleum ether was added, followed by dilute hydrochloric acid. The organic layer was separated, washed with dilute hydrochloric acid, then brine, dried and the solvent removed. The residue was mixed with petroleum ether and allowed to stand several days. After filtration, the filtrate was evaporated, giving 46.6 g of the desired compound as an oil, which was used in Example 9 without further purification.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with dilute hydrochloric acid
  4. dry with materialbrine, dried
  5. customthe solvent removed
  6. additionThe residue was mixed with petroleum ether
  7. waitto stand several days
  8. filtrationAfter filtration
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e3c7dc5c900f47a0bf306c2a733919df
Source dataset
uspto-grants-1989_05
Patent number
US04827011

Reaction notes

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