N,N-Dimethylaniline → 4-(6-Acryloyloxyhexyloxy)cinnamic acid

HRID 970248Notes

Reaction equation

HRID 970248 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:19]=[CH:18][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1.CN(C)C1C=CC=CC=1.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>O1CCOCC1>[C:29]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[CH:18][CH:19]=1)(=[O:32])[CH:30]=[CH2:31]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 13140Acryloyl chlorideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 673232894-(6-Hydroxyhexyloxy)cinnamic acid

Product 1

HCID 600674344-(6-Acryloyloxyhexyloxy)cinnamic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 21.15 g (0.08 mole) of 4-(6-hydroxyhexyloxy)cinnamic acid (13), 11.63 g (0.096 mole) of N,N-dimethylaniline 8.69 g (0.096 mole) of acryloyl chloride, 0.05 g of 2,6-di-t-butyl-4-methylphenol and 60 ml of 1,4-dioxane was heated at 60° C. under a nitrogen atmosphere. After 2 hours heating at 60° C. the mixture was filtered and dropped under stirring into a mixture of 1000 ml of water, 400 g of ice and 10 ml of 2.4 N hydrochloric acid. The solid precipitate was filtered off and recrystallized from 350 ml of ethanol. The solid was dried in a desiccator over silica gel. Yield 19.7 g (77.3%).

Workup

  1. temperatureAfter 2 hours heating at 60° C. the mixture
  2. filtrationwas filtered
  3. additiondropped
  4. filtrationThe solid precipitate was filtered off
  5. customrecrystallized from 350 ml of ethanol
  6. customThe solid was dried in a desiccator over silica gel

Sources & evidence

ORD record
ord-a29c7c72584142eb9d482b6096f12b91
Source dataset
uspto-grants-2007_12
Patent number
US07311948B2

Reaction notes

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