Isatoic Anhydride → 2-Amino-benzoic acid 2,4,6,8-tetramethyl-nonyl ester

HRID 61322Notes

Reaction equation

HRID 61322 reaction equation
[CH3:1][CH:2]([CH2:5][CH:6]([CH3:14])[CH2:7][CH:8]([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][OH:4].[C:15]12[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=1)[NH:20]C(=O)O[C:16]2=[O:17]>>[CH3:1][CH:2]([CH2:5][CH:6]([CH3:14])[CH2:7][CH:8]([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][O:4][C:16](=[O:17])[C:15]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:20]

Participants

3

Reactant 2

HCID 8359Isatoic AnhydrideHCID 131090222,4,6,8-Tetramethyl-nonan-1-ol

Product 1

HCID 666712462-Amino-benzoic acid 2,4,6,8-tetramethyl-nonyl esterYield 93.3%

Conditions

Temperature
120 °C

Procedure

A one liter, four necked, round bottom flask, equipped with an overhead stirrer, sub-surface gas inlet tube, thermowell, Dean-Stark trap, and Friedrick's condenser, is charged with 313.4 grams (1.56 moles) of 2,4,6,8-tetramethyl-nonan-1-ol. The flask is purged with nitrogen and warmed to 120 degrees C. 3.7 grams (46 mmoles) of a 50 percent by weight solution of NaOH in water is added drop-wise over 1 minute. The mixture is stirred at 120 degrees C. for 1 hour and water is collected in the Dean-Stark trap. 250 grams of isatoic anhydride (1.53 moles) is added portion-wise, supra-surface, over a period of 50 minutes. The mixture is stirred at 145 degrees C. for 6 hours. 9 grams of Fax-5 filter aid is added to the flask and stirred. The mixture is filtered and cooled to yield 456 grams of the product, in the form of a brown liquid. The product has a TBN, by ASTM D2896, of 150.

Workup

  1. customA one liter, four necked, round bottom flask, equipped with an overhead stirrer, sub-surface gas inlet tube
  2. customThe flask is purged with nitrogen
  3. addition3.7 grams (46 mmoles) of a 50 percent by weight solution of NaOH in water is added drop-wise over 1 minute
  4. customwater is collected in the Dean-Stark trap
  5. waitsupra-surface, over a period of 50 minutes
  6. stirringThe mixture is stirred at 145 degrees C
  7. waitfor 6 hours
  8. addition9 grams of Fax-5 filter aid is added to the flask
  9. stirringstirred
  10. filtrationThe mixture is filtered
  11. temperaturecooled

Sources & evidence

ORD record
ord-4f90feb0f6134402bc64ba8314ef3706
Source dataset
uspto-grants-2016_09
Patent number
US09441180B2

Reaction notes

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