N,N-Dimethylaniline → (4-(6-Acryloyloxyhexyloxy)phenyl)propionic acid
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.CN(C)C1C=CC=CC=1.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31].O>O1CCOCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[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:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1)(=[O:32])[CH:30]=[CH2:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
(4-(6-Hydroxyhexyloxy)phenyl)propionic acid (200 g), N,N-dimethylaniline (100 g) and BHT (0.3 g) were dissolved in dioxane (1,000 mL). Acrylic acid chloride (74.3 g) was added dropwise thereto over 10 minutes, followed by agitating at 60° C. for 5 hours. The reaction solution was poured into water, to which ethyl acetate was added, followed by agitating. The ethyl acetate layer was separated, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off from the ethyl acetate layer to obtain a solid product. The solid product was dissolved in toluene and reprecipitated by pouring into a large amount of heptane to obtain 213 g of (4-(6-acryloyloxyhexyloxy)phenyl)propionic acid. (Melting point: 64 to 68° C.)
Workup
- additionwas added
- stirringby agitating
- customThe ethyl acetate layer was separated
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off from the ethyl acetate layer
- customto obtain a solid product
- customreprecipitated
- additionby pouring into a large amount of heptane
Sources & evidence
- ORD record
- ord-0052e64c7fd14160996ec32c1c2a1f68
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378135B2
Reaction notes
Loading…