Acetic Acid → HCID 12902865, compound

HRID 262250Notes

Reaction equation

HRID 262250 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=4)[C:11]=3[CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:25]([O-:30])([N+]([O-])=O)=[O:26].C(O)(=O)C>ClCCl>[N+:25]([C:13]1[O:14][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:24][C:11]=2[C:12]=1[C:15]1[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:22][CH:23]=1)([O-:30])=[O:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 25352Nitrogen oxide (N2O4)HCID 12902864HCID 12902864, compound

Product 1

HCID 12902865HCID 12902865, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.2 g. of the product of step D, 2 g. of dinitrogen tetraoxide, 1 ml. of acetic acid and 200 ml. of dichloromethane is stirred at 20° C. for 16 hours, washed with water and evaporated. The residue is treated with cold 5 percent sodium hydroxide solution, then acidified with 6N hydrochloric acid. The solid residue is separated and recrystallized from N,N-dimethylformamide to provide 4-(2-nitro-5-phenylbenzofuran-3-yl)benzoic acid, m.p. 235°-249° C.

Workup

  1. additionA mixture of 3.2 g
  2. washwashed with water
  3. customevaporated
  4. additionThe residue is treated with cold 5 percent sodium hydroxide solution
  5. customThe solid residue is separated
  6. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-998572f4a8fb42e1b89be333120304cb
Source dataset
uspto-grants-1979_05
Patent number
US04153721

Reaction notes

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