HCID 59277551, compound → 3-Chloro-2-propoxybenzaldehyde

HRID 1362273Notes

Reaction equation

HRID 1362273 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH2:11][CH2:12][CH3:13])=[C:4]([CH2:8][OH:9])[CH:5]=[CH:6][CH:7]=1>C1C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[C:3]([O:10][CH2:11][CH2:12][CH3:13])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 59277551HCID 59277551, compound

Product 1

HCID 592775713-Chloro-2-propoxybenzaldehydeYield 38%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

MnO2 (3.40 g, 39.2 mmol) was added to a stirring solution of (3-chloro-2-propoxyphenyl)methanol (1.12 g, 5.60 mmol) in benzene (54 mL) under N2. After stirring for 48 h, the solution was filtered over diatomaceous earth, the pad rinsed with CH2Cl2 (100 mL), and the solution concentrated to a clear oil. Purification by column chromatography (silica gel, hexanes/EtOAc, 98:2) gave the title compound (0.42 g, 38%) as a clear oil: 1H NMR (300 MHz, DMSO-d6) δ 10.27 (s, 1H), 7.85 (d, J=1.6 Hz, 1H), 7.73 (d, J=1.6 Hz, 1H), 7.32 (t, J=7.8 Hz, 1H), 4.04 (t, J=6.4 Hz, 2H), 1.85-1.78 (m, 2H), 1.03 (t, J=7.3 Hz, 3H).

Workup

  1. filtrationthe solution was filtered over diatomaceous earth
  2. washthe pad rinsed with CH2Cl2 (100 mL)
  3. concentrationthe solution concentrated to a clear oil
  4. customPurification by column chromatography (silica gel, hexanes/EtOAc, 98:2)

Sources & evidence

ORD record
ord-c0820065571e486f9186f23bb3802eb1
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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