Selenium Dioxide → 4-Benzyloxy-3-hydroxymethylphenylglyoxal

HRID 1906969

Reaction equation

HRID 1906969 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[CH2:18][OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Se](=O)=[O:21]>O.O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH:16]=[O:21])=[O:17])=[CH:11][C:10]=1[CH2:18][OH:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 129693231-[3-(Hydroxymethyl)-4-(phenylmethoxy)phenyl]ethanone

Product 1

HCID 201341664-Benzyloxy-3-hydroxymethylphenylglyoxal

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(4-Benzyloxy-3-hydroxymethylphenyl)ethanone (10.4 g) was added portionwise to a stirred solution of selenium dioxide (5.5 g) in water (0.9 ml) and dioxan (100 ml) at 60 °. The mixture was stirred under reflux for 4 hours, filtered whilst hot and allowed to cool. The solid was collected and recrystallised from dioxan as a dimer, mp 180°-181° (7.7 g). (d6DMSO) 5.13 (1H, s), 4.94 (1H, s), 4.72 (2H, s), 3.42 (1H, d, J=10 Hz), 3.24 (1H, d, J=10 Hz), 2.72 (1H, m), 2.54 (5H, m), 2.04 (1H, m), 1.46 (1H, m).

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationfiltered whilst hot and
  3. temperatureto cool
  4. customThe solid was collected
  5. customrecrystallised from dioxan as a dimer, mp 180°-181° (7.7 g)

Sources & evidence

ORD record
ord-f9147e95a14c4abfa2bab9bcfe1bd4f4
Source dataset
uspto-grants-1987_03
Patent number
US04654371

Linked notes

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