Hydrochloric Acid → HCID 22006866, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[OH:15].[C:16](=[O:19])([O-])[O-].[K+].[K+].[CH3:22][N:23](C)[CH:24]=[O:25].Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[O:15][CH2:9][CH2:10][CH2:11][CH2:22][N:23]1[C:24](=[O:25])[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=[C:2]2[C:16]1=[O:19]Participants
Procedure
A mixture of 9.1 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 8.9 g of N-(4-bromoethyl)phthalimide, 4.4 g of potassium carbonate and 100 ml of N,N-dimethylformamide was stirred at room temperature for 24 hours. The reaction mixture was poured into ice water and made weak acidic by the addition of 10% hydrochloric acid, after which 200 ml of ethyl acetate was added for extraction. The ethyl acetate layer was successively washed with 10% hydrochloric acid and saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated to give crude crystals. The crude crystals were washed with n-hexane and then dried under reduced pressure, which afforded 14.5 g of 3,5-dichloro-4-(4-phthalimidobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (94% yield).
Workup
- washThe ethyl acetate layer was successively washed with 10% hydrochloric acid and saturated saline solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customto give crude crystals
- washThe crude crystals were washed with n-hexane
- customdried under reduced pressure, which
Sources & evidence
- ORD record
- ord-5bf6ac80af44428196a8490b20184fd2
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06214835B1
Reaction notes
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