4-Hydroxybenzoic Acid → 4,4'-Dihydroxybenzanilide

HRID 885091Notes

Reaction equation

HRID 885091 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.Cl>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 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

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 EDCl (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-470cc161dc0c45cd9d9fe501fc155e01
Source dataset
uspto-grants-2012_08
Patent number
US08242144B2

Reaction notes

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