Ethanol → HCID 5370806, compound

HRID 879918Notes

Reaction equation

HRID 879918 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[Na+].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O-:23])=[O:22])=[CH:16][CH:15]=1.O.CCO>C(OC(=O)C)(=O)C>[Br:13][C:14]1[CH:15]=[CH:16][C:17](/[C:20](=[CH:6]\[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])/[C:21]([OH:23])=[O:22])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 111012-NitrobenzaldehydeHCID 23673220HCID 23673220, compound

Product 1

HCID 5370806HCID 5370806, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

64.7 g (0.43 mol) of 2-nitrobenzaldehyde and 105.7 g (0.43 mol) of 4-bromophenylacetic acid sodium salt are dissolved in 500 ml of acetic anhydride and stirred at 80° C. for 2 h. When the reaction is complete, the mixture is extended with 1000 ml of water and 750 ml of EtOH and heated to 110° C., and, after 20 min, the orange solid is filtered off with suction, washed with water and MeOH and dried, giving 107 g (71.8%) of a yellow powder.

Workup

  1. temperatureheated to 110° C.
  2. waitafter 20 min
  3. filtrationthe orange solid is filtered off with suction
  4. washwashed with water and MeOH
  5. customdried

Sources & evidence

ORD record
ord-9ebea307b4e347a5940025823d6a295e
Source dataset
uspto-grants-2015_03
Patent number
US08993123B2

Reaction notes

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