Hydrochloric Acid → 4-(Benzyloxy)-3-nitrobenzoic acid

HRID 1360254Notes

Reaction equation

HRID 1360254 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([N+:18]([O-:20])=[O:19])[CH:5]=1.CO.[OH-].[K+].Cl>O1CCCC1>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][C:6]=1[N+:18]([O-:20])=[O:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 289857Methyl 4-benzyloxy-3-nitrobenzoate

Product 1

HCID 161247254-(Benzyloxy)-3-nitrobenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution the crude 4-benzyloxy-3-nitro-benzoic acid methyl ester from the previous step in tetrahydrofurane (150 mL) and MeOH (600 mL) was treated with KOH 3N (152 mL) and stirred at room temperature for 18 hours. The mixture was acidified with HCl 3N. The precipitate thus formed was filtered, washing with MeOH/water 1:1 and dried under vacuum. 4-Benzyloxy-3-nitro-benzoic acid (42 g, 95% over two steps) was obtained as a white solid, which was used crude in the following reaction.

Workup

  1. customThe precipitate thus formed
  2. filtrationwas filtered
  3. washwashing with MeOH/water 1:1
  4. customdried under vacuum

Sources & evidence

ORD record
ord-67d2cc2522e543f08b13be6214d4fa13
Source dataset
uspto-grants-2011_02
Patent number
US07879845B2

Reaction notes

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