1,2-Dimethoxyethane → HCID 86737116, compound

HRID 1759292Notes

Reaction equation

HRID 1759292 reaction equation
[CH2:1]([OH:14])[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].C[O:16][CH2:17][CH2:18]OC.C(N(CC)CC)C.[CH2:28]([N:46]=[C:47]=[O:48])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]>CCCCCCC>[CH2:28]([NH:46][C:47]([O:13][CH2:12][CH3:11])=[O:48])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].[CH2:28]([NH:46][C:47]([O:16][CH2:17][CH3:18])=[O:48])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].[CH2:12]([OH:13])[CH2:11][CH2:10][CH2:9][C:8]#[C:7][C:6]#[C:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:14]

Participants

6

Reactant 4

HCID 80711,2-Dimethoxyethane3×HCID 8471TriethylamineHCID 66988Octadecyl isocyanateHCID 5608785,7-Dodecadiyne-1,12-diol

Product 1

HCID 86737116HCID 86737116, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A mixture of 40 parts 5,7-dodecadiyne-1,12-diol, 215 parts 1,2-dimethoxyethane, 1 part dibutyltin-di-2-ethylhexanoate and 15 parts triethylamine was prepared and the resulting mixture was stirred vigorously. A solution of 133 parts n-octadecylisocyanate in 44 parts of 1,2-dimethoxyethane was added dropwise over a period of 60 min. The reaction temperature rose to 42° C. from 18° C. within 50 min. and then subsided. After the addition, 80 parts of 1,2-dimethoxyethane was then added to the reaction mixture and the mixture was stirred for an additional 2 hrs. To this mixture was added 1390 parts of heptane. The precipitate was collected by filtration, washed with petroleum ether (bp 30°-60° C.) and dried, giving 154.6 parts (99% yield) of desired product, mp 118°-119° C. Anal: calculated C50H92N2O4, C, 76.47%; H, 11.81%; N, 3.57%; found: C, 75.57%; H, 11.65%; N, 3.43%. IR (KBr pellet): 3330 cm-1 (N--H stretching), 2920+2850 cm-1 (C--H stretching), 1680 cm-1 (C=O), 1530 cm-1 (N--H bending), 1470 cm-1 (C--H), 1260 cm-1 (C--O--C stretching). Upon exposure to light, the crystals changed to blue, indicating the compound was solid state polymerizable.

Workup

  1. customwas prepared
  2. additionwas then added to the reaction mixture
  3. stirringthe mixture was stirred for an additional 2 hrs
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with petroleum ether (bp 30°-60° C.)
  6. customdried

Sources & evidence

ORD record
ord-e77e82c737df4e92b604167016465de3
Source dataset
uspto-grants-1982_07
Patent number
US04339951

Reaction notes

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