Methanol → HCID 19736313, compound

HRID 326209Notes

Reaction equation

HRID 326209 reaction equation
[CH2:1]([N:4]([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][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:49])C=1.C(OCC)(=O)C.CO>C(Cl)(Cl)Cl>[CH2:1]([N+:4]([O-:49])([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][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 19925741N-allyl-N,N-dioctadecylamine

Product 1

HCID 19736313HCID 19736313, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

Into a cooled solution of 5.0 g (9 mmol) of N-allyl-N,N-dioctadecylamine in 50 ml of chloroform at 0° C. under a nitrogen atmosphere is added dropwise with stirring a solution of 2.82 g (9 mmol) of 55% active m-chloroperbenzoic acid in 25 ml of chloroform. After the addition is complete (approximately 10 minutes), the resultant solution is allowed to warm to ambient temperature (about 22°-24° C.). The reaction is complete after about 2 hours when TLC analysis (silica gel, 19:1 v/v ethyl acetate:methanol)indicates the starting material has completely reacted. The reaction mixture is passed through a short column of basic alumina using chloroform as an eluent to give 5.2 g (quantitative yield) of the title compound as a white solid melting at 59°-64° C.

Workup

  1. additionAfter the addition
  2. custom(approximately 10 minutes)
  3. customhas completely reacted

Sources & evidence

ORD record
ord-00179d31146242c6b032c936111a7d0f
Source dataset
uspto-grants-1993_12
Patent number
US05268114

Reaction notes

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