Sodium Hydroxide → Benzoic acid, 2-nitro-3-(phenylmethoxy)-

HRID 1784890Notes

Reaction equation

HRID 1784890 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:25]([O-:27])=[O:26])=[C:11]([CH:22]=[CH:23][CH:24]=1)[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[C:10]([N+:25]([O-:27])=[O:26])=[C:11]([CH:22]=[CH:23][CH:24]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10594871Benzyl 3-benzyloxy-2-nitrobenzoate

Product 1

HCID 10802200Benzoic acid, 2-nitro-3-(phenylmethoxy)-Yield 101.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 20.7 g of benzyl 3-benzyloxy-2-nitrobenzoate were added 100 ml of ethanol and 120 ml of a 1N aqueous solution of sodium hydroxide and the mixture was stirred at room temperature for one night, at 60° C. for 3 hours and at 80° C. for 5 hours. After ethanol was evaporated in vacuo, the resulting aqueous solution was washed with ether and hydrochloric acid was added thereto. The resulting precipitate was collected by filtration and dried in vacuo to give 15.8 g of 3-benzyloxy-2-nitrobenzoic acid.

Workup

  1. customAfter ethanol was evaporated in vacuo
  2. washthe resulting aqueous solution was washed with ether and hydrochloric acid
  3. additionwas added
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0e5fe57f3f7d4301a11ddaebb78ff923
Source dataset
uspto-grants-2009_03
Patent number
US07504417B2

Reaction notes

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