(4-Fluoro-3-methoxyphenyl)methanol → 4-Fluoro-3-methoxybenzaldehyde

HRID 2102343Notes

Reaction equation

HRID 2102343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][CH3:11]>ClCCl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

4

Reactant 1

HCID 593590(4-Fluoro-3-methoxyphenyl)methanol

Product 1

HCID 27373584-Fluoro-3-methoxybenzaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(4-Fluoro-3-methoxyphenyl)methanol (5.00 g, 0.03 mol) and manganese dioxide (33.4 g, 0.38 mol) were stirred in dichloromethane (100 ml) under an atmosphere of nitrogen, at gentle reflux for 16 hours. The cooled reaction mixture was then filtered through arbacel and concentrated in vacuo to give the title compound as a white solid (4.18 g, 0.027 mol, 85%). 1H NMR (CDCl3, 400 MHz) δ: 3.96 (s, 3H), 7.23 (d, 1H), 7.43 (m, 1H), 7.50 (d, 1H), 9.91 (s, 1H). Mpt: 61-63° C. Analysis found C, 62.18; H, 4.54%. C8H7FO2 requires C, 62.34; H, 4.58%.

Workup

  1. temperatureat gentle reflux for 16 hours
  2. customThe cooled reaction mixture
  3. filtrationwas then filtered through arbacel
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d97d539b205a4da8b70adbf065de16e3
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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