Sodium Hydroxide → HCID 20061183, compound

HRID 1085305Notes

Reaction equation

HRID 1085305 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH:6]=[CH:7][C:8]([OH:10])=[O:9].S(O)(O)(=O)=O.ON.[OH-].[Na+].ONS(O)(=O)=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 159255Hydroxylamine, sulfate (1:1)HCID 170246Hydroxysulfamic acidHCID 542623503-Methoxy-4-nitrocinnamic acid

Product 1

HCID 20061183HCID 20061183, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

3-methoxy-4-nitrocinnamic acid (6.2 g) and 12.3 g of hydroxyamine sulfate were dissolved in 250 ml of water. To the solution was added 7.1 g of sodium hydroxide, and further alternately added a solution of 18 g of sodium hydroxide in water (27 ml) and 19.2 g of hydroxyamine-o-sulfonic acid little by little, maintaining the pH at 9. The mixture was stirred at 5° C. for 6 hours and then insoluble substances were removed by filtration. The resultant filtrate was cooled on ice and was added with 6 N sulfuric acid to adjust the pH to 2. Crystals formed were collected by filtration, washed with water and dried; 1.27 g of crystalline 3-(3-methoxy-4-nitrophenyl)propionic acid was thus obtained.

Workup

  1. temperaturemaintaining the pH at 9
  2. custominsoluble substances were removed by filtration
  3. temperatureThe resultant filtrate was cooled on ice
  4. additionwas added with 6 N sulfuric acid
  5. customCrystals formed
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-04e625dccfb4418b84640840fce26ffb
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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