Water → HCID 54099002, compound

HRID 868203Notes

Reaction equation

HRID 868203 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].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([OH:23])=[O:22].C(N(C(C)C)CC)(C)C.O>C(OC(=O)C)(=O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[CH:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[C:21]([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 71342-Methoxyphenylacetic acidHCID 111012-NitrobenzaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 54099002HCID 54099002, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
60 °C

Procedure

25 g of 2-nitrobenzaldehyde, 28 g of 2-methoxyphenylacetic acid and 0.16 mol of diisopropylethylamine are boiled under reflux in 90 ml of acetic anhydride under nitrogen for 8 hours. After cooling to 60° C. , the mixture is poured onto 200 ml of hot water. The mixture is stirred for a further 2 hours, while cooling, and the product is filtered off with suction and washed with a little cold ethanol. Recrystallization from ethanol gives 38.7 g of the title compound of melting point 217°-219° C.

Workup

  1. temperaturewhile cooling
  2. filtrationthe product is filtered off with suction
  3. washwashed with a little cold ethanol
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-07d8f9ff693345d285ad1794c399bc87
Source dataset
uspto-grants-1988_10
Patent number
US04778793

Reaction notes

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