1-Propanol → HCID 21520622, compound

HRID 1282948Notes

Reaction equation

HRID 1282948 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([C:19]([OH:21])=[O:20])[C:17]=1[OH:18])[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].S(=O)(=O)(O)O.[OH-].[Na+].[CH2:29](O)[CH2:30][CH3:31]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([C:19]([O:21][CH2:29][CH2:30][CH3:31])=[O:20])[C:17]=1[OH:18])[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13]

Participants

5

Reactant 4

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21520617HCID 21520617, compound

Product 1

HCID 21520622HCID 21520622, compoundYield 54.5%

Procedure

3'-Bromo-5'-carboxy-2,4'-dihydroxybenzanilide (1.0 g.) described in Example 4 was dissolved in n-propanol (50 ml.), and after adding conc. sulfuric acid (1 ml.) the solution was refluxed for 8 hours. After neutralizing with sodium hydroxide solution, the reaction solution was evaporated to dryness and the residue was washed with 5% sodium bicarbonate solution and recrystallized from aqueous acetone to give 3'-bromo-2,4'-dihydroxy-5'-n-propyloxycarbonylbenzanilide (0.61 g.). Yield: 54.5% Melting point 198°-200° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customthe reaction solution was evaporated to dryness
  3. washthe residue was washed with 5% sodium bicarbonate solution
  4. customrecrystallized from aqueous acetone

Sources & evidence

ORD record
ord-cd43419f213a45edbbcc8760a32acb3a
Source dataset
uspto-grants-1976_08
Patent number
US03973038

Reaction notes

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