Sodium Hydroxide → HCID 69256238, compound

HRID 898359Notes

Reaction equation

HRID 898359 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])=[C:4]([OH:17])[CH:3]=1.[OH-].[Na+:19]>CC(C)=O>[OH:17][C:4]1[CH:3]=[CH:2][CH:16]=[CH:15][C:5]=1[C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([O-:14])=[O:13])=[O:7].[Na+:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 98815804-(4-Chloro-2-hydroxybenzamido)butanoic acid

Product 1

HCID 69256238HCID 69256238, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A 22 L, five neck round bottom flask, was equipped with an overhead stirrer, reflux condenser, thermocouple temperature read out, and heating mantle. The following reaction was run under a dry nitrogen atmosphere. Reagent acetone (13000 mL) and 4-[(4-chloro-2-hydroxy-benzoyl)amino]butanoic acid (500.0 g, 1.94 mol) were charged to the reactor and stirring was started. The reaction slurry was heated to 50° C. until a hazy brown solution was obtained. The warm solution was pumped through a warm pressure filter dressed with Whatman #1 paper into a clean 22 L reactor. The clear yellow filtrate was heated to 50° C. while stirring. Sodium hydroxide solution (50% aqueous; 155 g, 1.94 mol) was charged to the reactor while maintaining vigorous agitation. After the base addition was complete, the reactor was heated to reflux (60° C.) for 2.5 hours and then allowed to cool slowly to ambient temperature. The product was isolated by vacuum filtration through a sintered glass funnel and dried in a vacuum oven at 50° C. for 24 hours to give 527.3 g of sodium 4-[(2-hydroxybenzoyl)amino]butanoate as an off-white solid. The yield was 97.2%.

Workup

  1. customA 22 L, five neck round bottom flask, was equipped with an overhead stirrer
  2. temperaturereflux condenser
  3. temperatureheating mantle
  4. customThe following reaction
  5. customwas obtained
  6. filtrationfilter
  7. customdressed with Whatman #1 paper into a clean 22 L reactor
  8. temperatureThe clear yellow filtrate was heated to 50° C.
  9. stirringwhile stirring
  10. temperaturewhile maintaining vigorous agitation
  11. additionAfter the base addition
  12. temperaturethe reactor was heated
  13. temperatureto reflux (60° C.) for 2.5 hours
  14. temperatureto cool slowly to ambient temperature
  15. customThe product was isolated by vacuum filtration through a sintered glass funnel
  16. customdried in a vacuum oven at 50° C. for 24 hours

Sources & evidence

ORD record
ord-9e50ee4b328f45e1a675459386c7d598
Source dataset
uspto-grants-2008_04
Patent number
US07351741B2

Reaction notes

Loading…