N,N-Dimethylaniline → HCID 69250913, compound

HRID 2223994Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([F:18])[CH:10]=1.CN(C)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[O:28]1C[CH2:31][CH2:30][CH2:29]1.C(Cl)(=O)C=C>C(C1C(O)=C(CCCC)C=C(C)C=1)CCC.O>[C:29]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:21][O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([F:18])[CH:10]=1)(=[O:28])[CH:30]=[CH2:31]

Participants

Conditions

Temperature: 60 °C

Procedure

Under a nitrogen atmosphere, 4-(6-hydroxyhexyloxy)-2-fluorobenzoic acid (189 g), N,N-dimethylaniline (133 g) and 2,6-dibutyl-p-cresol (0.80 g) were added to tetrahydrofuran (500 mL). Acrylic acid chloride (100 g) was added dropwise thereto, followed by agitating at 60° C. for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with hydrochloric acid, a saturated sodium hydrogencarbonate aqueous solution and water, and after drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from ethanol to obtain 4-(6-acryloylhexyloxyhexyloxy)-2-fluorobenzoic acid (141 g).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with hydrochloric acid
dry with materiala saturated sodium hydrogencarbonate aqueous solution and water, and after drying over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-ca72d716246f4bfab9b90c9e30af08c1
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378135B2

Reaction notes

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