Ethanol → HCID 54389232, compound

HRID 2107934Notes

Reaction equation

HRID 2107934 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].N1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH2:20]([C:28]1C=C[C:31]([CH:32]=[S:33])=[CH:30][CH:29]=1)[CH2:21][CH2:22]CCCCC.[CH2:36](O)C>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:15]2[CH:36]=[CH:19][C:18]([S:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:20][CH2:21][CH3:22])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 4661(4-Nitrophenyl)acetic acidHCID 8082PiperidineHCID 23044870HCID 23044870, compound

Product 1

HCID 54389232HCID 54389232, compound

Conditions

Temperature
120 °C

Procedure

A one liter two-neck flask equipped with a mechanical stirrer is charged with 4-nitrophenylacetic acid (90.5 g, 0.5 mole). The stirring action is commenced, and piperidine (46 g, 0.55 mole) is added dropwise. Heat is applied to the flask, and when the reaction medium begins to turn pink, 4-n-octylthiobenzaldehyde (125 g, 0.5 mole) is added. The reaction mixture is heated at 120° C. for 7 hours. At the end of this period, the reaction mixture is poured into a two liter volume of cold ethanol. The resultant yellow precipitate is collected, and recrystallized from ethanol to provide liquid crystalline 4-nitro-4'-octylthiostilbene, melting at 53° C. and clearing at 72° C.

Workup

  1. customA one liter two-neck flask equipped with a mechanical stirrer
  2. temperatureHeat
  3. customThe resultant yellow precipitate is collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-739f191736904dd7952cdc67254d21e5
Source dataset
uspto-grants-1990_06
Patent number
US04937017

Reaction notes

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