Sodium Hydroxide → HCID 70627959, compound

HRID 866735Notes

Reaction equation

HRID 866735 reaction equation
[C:1]([N:5]=[N:6][C:7]([S:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=1)([CH3:17])[CH2:8][CH2:9][C:10]([O:12]CCCC)=[O:11])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O>[C:1]([N:5]=[N:6][C:7]([S:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=1)([CH3:17])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70627963HCID 70627963, compound

Product 1

HCID 70627959HCID 70627959, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 167 grams (0.412 moles) of n-butyl 4-t-butylazo-4-(p-t-butylthiophenoxy)valerate and 34.4 grams (0.43 moles) of 50% NaOH were stirred in a 500 ml. round bottom flask, equipped with a condenser, for 4 hours at 85°-90° C. The reaction mixture was then cooled to room temperature and poured into 400 ml. water. The aqueous solution was extracted with 100 ml. of pentane to remove any unreacted ester and butyl alcohol and the pentane layer discarded. The aqueous layer was acidified to a pH of 3. The desired acid precipitated out of solution, was filtered off, washed with water and air dried. The dry product weighed 107 grams (74% yield).

Workup

  1. customround bottom flask, equipped with a condenser, for 4 hours at 85°-90° C
  2. additionpoured into 400 ml
  3. extractionThe aqueous solution was extracted with 100 ml
  4. customof pentane to remove any unreacted ester and butyl alcohol
  5. customThe desired acid precipitated out of solution
  6. filtrationwas filtered off
  7. washwashed with water and air
  8. customdried

Sources & evidence

ORD record
ord-8d630a1759894f259088fa68d3d22303
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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