Acrylonitrile → HCID 66571292, compound

HRID 705443Notes

Reaction equation

HRID 705443 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:8]=2[C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:11])[CH2:2][CH2:3][CH3:4].[C:26](#[N:29])[CH:27]=[CH2:28].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>>[N+:23]([C:20]1[CH:21]=[CH:22][C:7]2[O:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[C:9]([C:10]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:28][CH2:27][C:26]#[N:29])=[CH:16][CH:17]=3)=[O:11])[C:8]=2[CH:19]=1)([O-:25])=[O:24]

Participants

4

Reactant 3

HCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 11473234(2-Butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone

Product 1

HCID 66571292HCID 66571292, compound

Conditions

Temperature
82.5 °C

Procedure

27.8 g of (2-butyl-5-nitro-1-benzofur-3-yl)-(4-hydroxyphenyl)methanon (VIII), 43.5 g of acrylonitrile and 3.8 g of Triton B (benzyltrimethylammonium hydroxide) are added and heated under stirring to 80-85° C. and stirred at this temperature for 48 hours. After cooling the reaction mixture to room temperature it is evaporated and the acrylonitrile is recovered for the next trial. To the residue 150 ml of dichloromethane is added and washed with 3×80 ml of sodium hydroxide of 5%. From the sodium hydroxide solution 16.2 g of starting (2-butyl-5-nitro-1-benzofur-3-yl)-(4-hydroxyphenyl)methanon is recovered.

Workup

  1. temperatureheated
  2. stirringstirred at this temperature for 48 hours
  3. temperatureAfter cooling the reaction mixture to room temperature it
  4. customis evaporated
  5. customthe acrylonitrile is recovered for the next trial
  6. additionTo the residue 150 ml of dichloromethane is added
  7. washwashed with 3×80 ml of sodium hydroxide of 5%
  8. customFrom the sodium hydroxide solution 16.2 g of starting (2-butyl-5-nitro-1-benzofur-3-yl)-(4-hydroxyphenyl)methanon is recovered

Sources & evidence

ORD record
ord-9b74aebdf28148d6b6ac3ff7163f41cf
Source dataset
uspto-grants-2015_11
Patent number
US09174959B2

Reaction notes

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