Acetic Anhydride → HCID 54074224, compound

HRID 1763169Notes

Reaction equation

HRID 1763169 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=O)[CH3:2].[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[CH2:18])=[CH:13][CH:12]=1)[CH3:9].[Cl:28][C:29]1[C:30]([Cl:42])=[C:31]([Cl:41])[C:32]([Cl:40])=[C:33]2[C:38](=O)[O:37][C:35](=[O:36])[C:34]=12.[OH-].[Na+]>O.ClC1C=CC=CC=1Cl>[CH3:27][N:25]([CH3:26])[C:22]1[CH:21]=[CH:20][C:19]([C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:8][CH3:9])=[CH:12][CH:13]=2)=[CH:18][C:38]2([CH:18]=[C:17]([C:14]3[CH:13]=[CH:12][C:1]([O:4][CH2:5][CH3:6])=[CH:2][CH:15]=3)[C:19]3[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=3)[C:33]3[C:34](=[C:29]([Cl:28])[C:30]([Cl:42])=[C:31]([Cl:41])[C:32]=3[Cl:40])[C:35](=[O:36])[O:37]2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8326Tetrachlorophthalic anhydrideHCID 14798Sodium HydroxideHCID 145122554-[1-(4-Ethoxyphenyl)ethenyl]-N,N-dimethylaniline

Product 1

HCID 54074224HCID 54074224, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

Into a mixture of 25 ml of acetic anhydride and 75 ml of o-dichlorobenzene, 13.4 g of 1-(p-ethoxyphenyl)-1-(p-dimethylaminophenyl)ethylene (melting at 110°-111° C.) and 21.5 g of tetrachlorophthalic anhydride were added and the mixture was stirred for 6 hours at 120° C. After adding the reaction mixture into 200 ml of water and making the mixture alkaline by 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 acetone while purifying with activated carbon to obtain 16.2 g of pale yellow crystals in a yield of 80.8%.

Workup

  1. additionwere added
  2. extractionthe alkaline mixture was extracted with 70 ml of toluene
  3. customThe solid matter obtained
  4. distillationby distilling off toluene from the extract
  5. customwas recrystallized from acetone
  6. customwhile purifying with activated carbon

Sources & evidence

ORD record
ord-ec5b4c14384a4b7198296d0079296fdd
Source dataset
uspto-grants-1989_05
Patent number
US04835291

Reaction notes

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