Butyric Acid → 4'-Hydroxybutyranilide

HRID 503664Notes

Reaction equation

HRID 503664 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](O)(=[O:13])[CH2:10][CH2:11][CH3:12].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:9]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)(=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 264Butyric AcidHCID 4034-AminophenolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 668744'-Hydroxybutyranilide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-aminophenol (550 mg; 5 mmol) is added to a solution of butyric acid (1.4 mL; 15 mmol) in DCM (20 mL) at room temperature and stirred vigorously. To this solution DCC (2.48 g; 12 mmol) is added followed by DMAP (24 mg) and the contents stirred overnight at room temperature. The reaction mixture is then filtered and washed with DCM. The filtrate is concentrated and redissolved in methanol, added with 10% aqueous sodium bicarbonate solution and stirred vigorously until diacylated byproduct disappeared (as detected by LC-MS) to yield 4-butyramidophenol as the only product. The product was used for further transformation without further purification.

Workup

  1. stirringthe contents stirred overnight at room temperature
  2. filtrationThe reaction mixture is then filtered
  3. washwashed with DCM
  4. concentrationThe filtrate is concentrated
  5. dissolutionredissolved in methanol
  6. additionadded with 10% aqueous sodium bicarbonate solution
  7. stirringstirred vigorously until diacylated byproduct

Sources & evidence

ORD record
ord-ac6353b317e04aec904eccd77aa26a4e
Source dataset
uspto-grants-2010_08
Patent number
US07776919B2

Reaction notes

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