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

HRID 1792390
Notes
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Reaction equation

HRID 1792390 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 220332203-[7-Methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]benzyl alcohol

Product 1

HCID 220330033-[7-Methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

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

  1. filtrationwas then filtrated over silica gel
  2. washwashed with several times with methylene chloride
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes