Acetic Acid → HCID 13066648, compound

HRID 1606636Notes

Reaction equation

HRID 1606636 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:38]=[CH:37][CH:36]=[CH:35][C:8]=1[C:9]([NH:11][C:12]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30]C(=O)C)=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])=[O:10])(=O)C.CO.C(O)(=O)C>O>[C:9]([NH:11][C:12]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:34])[C:24]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[OH:30])=[CH:18][C:13]=1[C:14]([OH:16])=[O:15])(=[O:10])[C:8]1[C:7](=[CH:38][CH:37]=[CH:36][CH:35]=1)[OH:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 13066645HCID 13066645, compound

Product 1

HCID 13066648HCID 13066648, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An aqueous solution of 4 g of sodium hydroxide in 10 ml of water was added to a mixture of 5.3 g of methyl 2,5-bis(2'-acetoxybenzamido)-benzoate obtained in Example 3 and 100 ml of methanol. The resulting mixture was stirred at room temperature for 20 - 30 hours and then poured into 500 ml of water containing 10 ml of acetic acid to precipitate crystals. The crystals were recovered by filtration, washed with water and recrystallized from a mixture of dioxane and water to yield 3.5 g of 2,5-bis(salicylamido)-benzoic acid having a melting point between 280° - 283°C (decomposition).

Workup

  1. customto precipitate crystals
  2. filtrationThe crystals were recovered by filtration
  3. washwashed with water
  4. customrecrystallized from a mixture of dioxane and water

Sources & evidence

ORD record
ord-e8a0884be8ac413ab687f757ef322dcc
Source dataset
uspto-grants-1976_04
Patent number
US03953496

Reaction notes

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