N,N-Diethylaniline → 3,4-Di-(6-acryloyloxyhexyloxy)benzoic acid

HRID 47152Notes

Reaction equation

HRID 47152 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[C:12]([OH:14])=[O:13].C(N(CC)C1C=CC=CC=1)C.C(C1[C:46]([OH:47])=[C:45]([C:48](C)(C)C)C=C(C)C=1)(C)(C)C.[C:53](Cl)(=[O:56])[CH:54]=[CH2:55]>O1CCOCC1>[C:53]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:46](=[O:47])[CH:45]=[CH2:48])[C:12]([OH:14])=[O:13])(=[O:56])[CH:54]=[CH2:55]

Participants

6

Reactant 4

HCID 7061N,N-DiethylanilineHCID 13140Acryloyl chlorideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 11302673HCID 11302673, compound

Product 1

HCID 113171823,4-Di-(6-acryloyloxyhexyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

13.6 g (0.04 mol) of 3,4-di-(6-hydroxyhexyloxy)benzoic acid, 9.6 ml (0.06 mol) of N,N-diethylaniline and 100 mg of 2,6-di-tert-butyl-p-cresol as stabilizer are added to 150 ml of 1,4-dioxane and heated to 60° C. At 60° C., 6.9 ml (0.085 mol) of acryloyl chloride are added slowly such that the reaction temperature does not exceed 65° C. The reaction mixture is stirred for 2.5 h at 60° C. The solution is cooled to room temperature and poured onto ice water with stirring. A precipitate of 3,4-di-(6-acryloyloxyhexyloxy)benzoic acid is obtained which is separated by filtration, dried and recrystallized from 300 ml of isopropanol.

Workup

  1. customdoes not exceed 65° C
  2. temperatureThe solution is cooled to room temperature
  3. additionpoured onto ice water
  4. stirringwith stirring

Sources & evidence

ORD record
ord-361465357b144836a1136c1495d4053a
Source dataset
uspto-grants-2004_03
Patent number
US06699405B2

Reaction notes

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