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

HRID 478172Notes

Reaction equation

HRID 478172 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 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. The resulting precipitate was filtered 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 filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5a235702d5ce406081c1373ba5f83701
Source dataset
uspto-grants-2003_11
Patent number
US06642224B1

Reaction notes

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