Water → N,N,N-Trimethyl-1-adamantylammonium hydroxide

HRID 2201605Notes

Reaction equation

HRID 2201605 reaction equation
C[O:2]C(=O)[O-].[C:6]12([N+:16]([CH3:19])([CH3:18])[CH3:17])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.O.[OH-].[Ca+2].[OH-]>CO>[OH-:2].[C:6]12([N+:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:9][CH:8]([CH2:14]3)[CH2:7]1)[CH2:15]2

Participants

5

Reactant 3

HCID 962WaterHCID 6093208Calcium HydroxideHCID 67399232HCID 67399232, compound

Product 1

HCID 14475644N,N,N-Trimethyl-1-adamantylammonium hydroxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

Adamantyltrimethylammonium methylcarbonate (383 g, 1.42 mol) is added to water (1000 mL), followed by addition of calcium hydroxide (148 g, 2.0 mol). This addition is exothermic. The reaction mixture is then heated to reflux and the methanol produced is slowly distilled off until the vapor temperature is constant. The reaction mixture is then cooled slowly to 10° C. and the precipitated calcium carbonate and excess calcium hydroxide are filtered off on a Nutsche filter. The filter cake is washed with water (200 mL) and both the mother and wash filtrates are combined. The 1-adamantyltrimethylammonium hydroxide product yield is 1284 grams of solution with assay 20.2% w/w.

Workup

  1. additionThis addition
  2. temperatureThe reaction mixture is then heated
  3. temperatureto reflux
  4. distillationis slowly distilled off until the vapor temperature
  5. filtrationthe precipitated calcium carbonate and excess calcium hydroxide are filtered off on a Nutsche
  6. filtrationfilter
  7. washThe filter cake is washed with water (200 mL)
  8. washboth the mother and wash filtrates

Sources & evidence

ORD record
ord-d07b2dc5c5f141c4af169c13fa9597b7
Source dataset
uspto-grants-2016_06
Patent number
US09365490B2

Reaction notes

Loading…