4-Phenylbutyric Acid → HCID 20240405, compound

HRID 364147Notes

Reaction equation

HRID 364147 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[C:19]1([NH:25][OH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C1C=CC=CC=1.O1CCCCC1.C1COCC1.O.CCOC(C)=O.CN(C)C=O>[OH:26][N:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

10

Reactant 4

HCID 47754-Phenylbutyric AcidHCID 7518N-PhenylhydroxylamineHCID 8471TriethylamineHCID 65578Oxalyl chloride

Product 1

HCID 20240405HCID 20240405, compoundYield 58%

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 8894TetrahydropyranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirring solution of 3-phenylpropylcarboxylic acid (500 mg, 3.1 mmol) in 10 ml of dry benzene under argon was added oxalyl chloride (0.30 ml, 1.1 eq.). To this solution was added dimethylformamide dropwise in 10 minute intervals, until no gas was evolved and the solution turned slightly cloudy (2 drops). The mixture was stirred for 1 hour then reduced on the rotovap without heating. The crude product was diluted with 5 ml of tetrahydropyran and added dropwise to a 0° C. solution of N-phenylhydroxylamine (666 mg, 2 eq.) in 20 ml of THF:H2O (1:1) with triethylamine (0.85 ml, 2.0 eq.). The solution was stirred for 1 hour at 0° C. then allowed to warm to room temperature and stir overnight. The reaction mixture was diluted with EtOAc and the organic layer was washed with H2O, 1N HCl (2X), and brine, then dried over anhydrous MgSO4. Concentration in vacuo gave a white solid which was recrystallized from hot hexane/EtOAc, to give title product (451 mg, 58%) as a flat golden crystalline solid.

Workup

  1. temperaturewithout heating
  2. stirringThe solution was stirred for 1 hour at 0° C.
  3. stirringstir overnight
  4. washthe organic layer was washed with H2O, 1N HCl (2X), and brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationConcentration in vacuo
  7. customgave a white solid which
  8. customwas recrystallized from hot hexane/EtOAc

Sources & evidence

ORD record
ord-2f4d6ab2e94147048fa53740f0e5f72b
Source dataset
uspto-grants-1986_08
Patent number
US04604407

Reaction notes

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