Benzyl 4-hydroxyphenyl ketone → HCID 136332506, compound

HRID 2233417Notes

Reaction equation

HRID 2233417 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Cl.[O:18]([NH2:20])[CH3:19]>N1C=CC=CC=1>[CH3:19][O:18][N:20]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 75607Benzyl 4-hydroxyphenyl ketoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 136332506HCID 136332506, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(4-hydroxy-phenyl)-2-phenyl-ethanone (10.00 g, 47.12 mmol) was dissolved in pyridine (60 mL) and methoxylamine hydrochloride (5.90 g, 70.64 mmol) was added. The resulting reaction mixture was stirred at room temperature for 14 hours, and then concentrated. The solids were washed with ether, and the ether layers were combined and concentrated to afford the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 3.90 (s, 3 H) 4.06 (s, 2 H) 6.73 (d, J=8.21 Hz, 1 H) 7.18 (dt, J=15.46, 7.66 Hz, 2 H) 7.38-7.44 (m, 1H) 7.50 (d, J=7.92 Hz, 1 H) 7.81 (s, 2 H) 8.55-8.64 (m, 2 H).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated
  3. washThe solids were washed with ether
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-46036693d21a4cf6995c758fa1386396
Source dataset
uspto-grants-2010_05
Patent number
US07709507B2

Reaction notes

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