3-[7-Methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]benzyl alcohol → 3-[7-Methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]benzaldehyde

HRID 1792390Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([C:21]3[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=3)[CH2:24][OH:25])[CH:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:9][S:10]2)=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([C:21]3[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=3)[CH:24]=[O:25])[CH:8]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)[CH2:9][S:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 40 °C

Procedure

The mixture of 3-[7-methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]benzyl alcohol (358 mg, 0.912 mmol) and manganese(IV) oxide (634 mg, 7.296 mmol) in methylene chloride (80 ml) was stirred at 40° C. for 3 h. When the reaction was completed, methylene chloride was added to the reaction mixture, which was then filtrated over silica gel and washed with several times with methylene chloride. The organic layer was concentrated under reduced pressure to give 360 mg (quant.) of the title compound as a white crystal.

Workup

filtrationwas then filtrated over silica gel
washwashed with several times with methylene chloride
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-ef62e84dcdca4ffda1fe1b2c01035c6c
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074819B2

Reaction notes

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