4-Hydroxybenzoic Acid → 4,4'-Dihydroxybenzanilide

HRID 2260948Notes

Reaction equation

HRID 2260948 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.CCN=C=NCCCN(C)C>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 4034-AminophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 9504804,4'-DihydroxybenzanilideYield 34.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzoic acid (1.01 g, 7.31 mmol) and 4-aminophenol (1.19 g, 10.9 mmol) were dissolved in 15 mL of dry DMF. To the above solution EDCI (1.40 g, 7.31 mmoL) was added in one portion and the resulting mixture was stirred at rt overnight under nitrogen. The reaction mixture was then partitioned between EtOAc (200 mL) and water (200 mL). The organic layer was separated, washed consecutively with 1 N HCl, water, saturated sodium bicarbonate solution, water, and brine, and dried over MgSO4. Solvent was removed under reduced pressure and the crude product was purified by column chromatography using EtOAc in hexane as an eluent (10% to 20%) to give 580 mg (34% yield) of 4-hydroxy-N-(4-hydroxyphenyl)-benzamide. MS (ES) m/z: 230.04 (M+1).

Workup

  1. customThe reaction mixture was then partitioned between EtOAc (200 mL) and water (200 mL)
  2. customThe organic layer was separated
  3. washwashed consecutively with 1 N HCl, water, saturated sodium bicarbonate solution, water, and brine
  4. dry with materialdried over MgSO4
  5. customSolvent was removed under reduced pressure
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e413f568739645b2a2c5c47fc11a3307
Source dataset
uspto-grants-2010_12
Patent number
US07846915B2

Reaction notes

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