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

HRID 600224Notes

Reaction equation

HRID 600224 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-9e6234b5aebf4c60b818091ed9b7f852
Source dataset
uspto-grants-2011_03
Patent number
US07902188B2

Reaction notes

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