4-Hydroxymethyl-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine → 7-(4-Methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbaldehyde

HRID 1169377Notes

Reaction equation

HRID 1169377 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][CH2:5][O:6][C:7]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[CH:10][C:8]=2[CH:9]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH:12]=[CH:13][C:7]3[O:6][CH2:5][CH2:4][C:3]([CH:2]=[O:1])=[CH:9][C:8]=3[CH:10]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 229901384-Hydroxymethyl-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine

Product 1

HCID 229901807-(4-Methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbaldehydeYield 92.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a solution of 4-hydroxymethyl-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine (0.21 g) in dichloromethane (10 ml) were added manganese dioxide (687 mg), and the resulting mixture was stirred at room temperature for 3 hours. An insoluble material was removed by filtration, and the filtrate was evaporated to remove dichloromethane. The residue was recrystallized from ethyl acetate/hexane to obtain 7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbaldehyde (192 mg) as colorless crystals.

Workup

  1. customAn insoluble material was removed by filtration
  2. customthe filtrate was evaporated
  3. customto remove dichloromethane
  4. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-979a25437fd8450a9f1710f0bff2f484
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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