N,N-Dimethylaniline → (4-(6-Acryloyloxyhexyloxy)phenyl)propionic acid
Reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1.CN(C)C1C=CC=CC=1.O1CCOCC1>C1(C)C=CC=CC=1.CCCCCCC.C(OCC)(=O)C.O>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]([CH3:24])[C:21]([OH:23])=[O:22])=[CH:18][CH:19]=1)(=[O:4])[CH:2]=[CH2:3]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 60 °C
Procedure
Acrylic acid chloride (74.3 g) was dropped for 10 minutes to a mixture of (4-(6-hydroxyhexyloxy)phenyl)propionic acid (200 g), N,N-dimethylaniline (100 g), BHT (0.3 g), and dioxane (1,000 mL). After stirring at 60° C. for 5 hours, the reaction mixture was poured into water and stirred with addition of ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation from the ethyl acetate layer to obtain solids. The solids were dissolved in toluene and poured into plenty of heptane and re-precipitated to obtain (4-(6-acryloyloxyhexyloxy)phenyl)propionic acid (AK2: 213 g). Melting point: 64° C. to 68° C.
Workup
- washThe ethyl acetate layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed by distillation from the ethyl acetate layer
- customto obtain solids
- customre-precipitated
Sources & evidence
- ORD record
- ord-dc8752a737e04cf8b0d74078c20211cf
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393569B2
Reaction notes
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