Triethylamine → HCID 23369169, compound

HRID 1900534Notes

Reaction equation

HRID 1900534 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(C1C=CC(C)=C(O)C=1C(C)(C)C)(C)(C)C.[CH2:23]([OH:59])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH3:58].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:59][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH3:58])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 19351831HCID 19351831, compoundHCID 23369168HCID 23369168, compound

Product 1

HCID 23369169HCID 23369169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.87 g (0.018 mol) of methacrylyl chloride and a small amount of di-t-butylhydroxytoluene in methylene chloride are added to a solution of 8 g (0.0148 mol) of 11,14,17,20,23,26,29,32,35-Nonaoxahexatriacontan-1-ol and 1.82 g (0.018 mol) of triethylamine in 40 ml of methylene chloride at a temperature of -20° C. The mixture is stirred at room temperature for 12 hours, without cooling. The solvent is removed at room temperature and the crude product is worked up by flash chromatography over silica gel 60 (0.040-0.063 mm) using acetone/ether 50:50. The mobile phase is distilled off at room temperature and the product is obtained as a colorless liquid. 1HNMR: 1.2-1.8 ppm (m, 16H, (--CH2)8 --), 1.9 ppm (s, 1H, HO--), 3.4 ppm (s, 3H, --OCH3), 3.7 ppm (m, 34H, --(OCH2CH2)8 --O--),--(CH2)8 --CH2 --O--), 4.2 ppm (m, 2H, --COO--CH2 --CH 2 --), 5.5 ppm (s, 1H, H--CH=C(CH3)--COO--), 6.1 ppm (s, 1H, H--CH=C(CH3)--COO--). IR (film): 1700 cm-1 (C=O), 1620 cm-1 (C=C), 1110 cm-l (C--O).

Workup

  1. temperaturewithout cooling
  2. customThe solvent is removed at room temperature
  3. distillationThe mobile phase is distilled off at room temperature
  4. customthe product is obtained as a colorless liquid

Sources & evidence

ORD record
ord-675d59dd63564d279af1c696a6aad626
Source dataset
uspto-grants-1996_11
Patent number
US05576012

Reaction notes

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