Pyridine → HCID 70635582, compound

HRID 441437Notes

Reaction equation

HRID 441437 reaction equation
[Br-:1].[CH2:2]([N+:14]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[OH:23])([CH3:16])[CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:24](OC(=O)C)(=[O:26])[CH3:25].N1C=CC=CC=1>O>[Br-:1].[C:24]([O:23][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[N+:14]([CH3:15])([CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21418713HCID 21418713, compound

Product 1

HCID 70635582HCID 70635582, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.0 g of dodecyl(2-hydroxycyclohexyl)-dimethylammonium bromide prepared in Example 3, 5 ml of acetic anhydride and 5 ml of dry pyridine was allowed to stand at room temperature for about 16 hours. Twenty-five milliliters of water was added and the mixture allowed to stand for one hour. The solution was concentrated under reduced pressure at 50° using a rotary film evaporator. Two 20 ml portions of water were added successively to aid removal of pyridine, followed by absolute ethanol for final drying. The residue was 1.11 g of (2-acetoxycyclohexyl)(dimethyl)dodecylammonium bromide. The ir spectrum was consistent with the assigned structure and clearly showed esterification of the hydroxy group to have occurred.

Workup

  1. waitto stand for one hour
  2. concentrationThe solution was concentrated under reduced pressure at 50°
  3. customa rotary film evaporator
  4. additionTwo 20 ml portions of water were added successively
  5. customremoval of pyridine
  6. customfor final drying

Sources & evidence

ORD record
ord-7c58811923fa479ab3fd5517b96e3878
Source dataset
uspto-grants-1977_08
Patent number
US04040813

Reaction notes

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