Methacryloyl chloride → 4-(6-Methacryloxyhexyloxy)-4'-nitrostilbene

HRID 2073127Notes

Reaction equation

HRID 2073127 reaction equation
O1CCOCC1.[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[CH:17][CH:16]=1.[C:32](Cl)(=[O:36])[C:33]([CH3:35])=[CH2:34]>C(N(CC)CC)C>[C:32]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[CH:17][CH:16]=1)(=[O:36])[C:33]([CH3:35])=[CH2:34]

Participants

5

Reactant 3

HCID 13528Methacryloyl chloride2×HCID 312751,4-DioxaneHCID 539381646-{4-[2-(4-Nitrophenyl)ethenyl]phenoxy}hexan-1-OL

Product 1

HCID 542023444-(6-Methacryloxyhexyloxy)-4'-nitrostilbene

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To 500 ml of dry dioxane in a reaction flask are added 9.0 g of 4-(6-hydroxyhexyloxy)-4'-nitrostilbene and 5 g triethylamine. The solution is heated to 50° C., and 3.7 g of methacryloyl chloride is added dropwise. The reaction is stirred at 45°-50° C. for about 6 hours and an additional 3.7 g of methacryloyl chloride is added. The reaction mixture is stirred for about 10 hours at 50° C., the dioxane is removed and the resultant residue is slurried with water in a blender. The solid is filtered, washed with water, and dried. The crude product is recrystallized from ethanol, mp 90°-95° C.

Workup

  1. stirringThe reaction mixture is stirred for about 10 hours at 50° C.
  2. customthe dioxane is removed
  3. filtrationThe solid is filtered
  4. washwashed with water
  5. customdried
  6. customThe crude product is recrystallized from ethanol, mp 90°-95° C.

Sources & evidence

ORD record
ord-e7e31e01e7414addb39d2c576e7a6686
Source dataset
uspto-grants-1990_04
Patent number
US04915491

Reaction notes

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