Acetic Anhydride → 4,5,6,7-Tetrachloro-3,3-bis[2-[4-(dimethylamino)phenyl]-2-(4-methoxyphenyl)ethenyl]-1(3H)-isobenzofuranone

HRID 1763167Notes

Reaction equation

[C:1]([O:4][C:5](=O)[CH3:6])(=O)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([N:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=2)=[CH2:17])=[CH:12][CH:11]=1.[Cl:27][C:28]1[C:29]([Cl:41])=[C:30]([Cl:40])[C:31]([Cl:39])=[C:32]2[C:37](=O)[O:36][C:34](=[O:35])[C:33]=12.[OH-].[Na+]>O>[CH3:25][N:24]([CH3:26])[C:21]1[CH:20]=[CH:19][C:18]([C:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:15][CH:14]=2)=[CH:17][C:37]2([CH:17]=[C:16]([C:13]3[CH:14]=[CH:6][C:5]([O:4][CH3:1])=[CH:11][CH:12]=3)[C:18]3[CH:23]=[CH:22][C:21]([N:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=3)[C:32]3[C:33](=[C:28]([Cl:27])[C:29]([Cl:41])=[C:30]([Cl:40])[C:31]=3[Cl:39])[C:34](=[O:35])[O:36]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Into 25 ml of acetic anhydride, 13.0 g of 1-(p-methoxyphenyl)-1-(p-dimethylaminophenyl)ethylene and 9.3 g of tetrachlorophthalic anhydride were added and the mixture was stirred for 2 hours at 120° C. After adding the reaction mixture into 200 ml of water and making the mixture alkaline with sodium hydroxide, the alkaline mixture was extracted with 70 ml of toluene. The solid matter obtained by distilling off toluene from the extract was recrystallized from butanol while purifying with activated carbon to obtain 14.3 g of pale yellow crystals melting at 133°-135° C.

Workup

extractionthe alkaline mixture was extracted with 70 ml of toluene
customThe solid matter obtained
distillationby distilling off toluene from the extract
customwas recrystallized from butanol
customwhile purifying with activated carbon

Sources & evidence

ORD record: ord-862e6d96dd8c4563a955db92e4904f6c
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04835291

Reaction notes

Loading…