Water → HCID 12789562, compound

HRID 1732724Notes

Reaction equation

HRID 1732724 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[OH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.O>[N+](C1C=CC=CC=1)([O-])=O.[Cu]>[CH2:15]([O:14][C:12]([C:11]1[CH:10]=[CH:9][C:8]([O:7][C:8]2[CH:18]=[CH:17][CH:11]=[CH:10][C:9]=2[C:1]([OH:2])=[O:4])=[CH:18][CH:17]=1)=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 8434EthylparabenHCID 11430Potassium Carbonate2×

Product 1

HCID 12789562HCID 12789562, compoundYield 145.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7416NitrobenzeneSolvent

Procedure

Potassium carbonate (14 g) was added to a solution of 2-indobenzoic acid (50 g) in nitrobenzene (50 ml) at 140°-150° C. with stirring. The mixture was stirred for an additional 10 minutes after the addition. Then, ethyl 4-hydroxybenzoate (33.5 g), potassium carbonate (28 g) and copper (3 g) were added. The mixture was stirred at 150°-160° C. for 30 minutes and allowed to cool. After the addition of water, the mixture was filtered and the filtrate was acidified with concentrated hydrochloric acid. The precipitate was collected and recrystallized from dilute ethanol to give the title compound (42 g, 72%), m.p. 152°-153° C.

Workup

  1. stirringThe mixture was stirred for an additional 10 minutes
  2. additionafter the addition
  3. stirringThe mixture was stirred at 150°-160° C. for 30 minutes
  4. temperatureto cool
  5. filtrationthe mixture was filtered
  6. customThe precipitate was collected
  7. customrecrystallized from dilute ethanol

Sources & evidence

ORD record
ord-54dc4baba703474e939a09dbe855f6fd
Source dataset
uspto-grants-1980_12
Patent number
US04238620

Reaction notes

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