(2-Ethoxy-3-isopropylphenyl)methanol → 2-Ethoxy-3-isopropylbenzaldehyde

HRID 1362287Notes

Reaction equation

HRID 1362287 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:13][OH:14])[CH3:2]>C1C=CC=CC=1.O=[Mn]=O>[CH2:1]([O:3][C:4]1[C:9]([CH:10]([CH3:11])[CH3:12])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]=[O:14])[CH3:2]

Participants

4

Reactant 1

HCID 59277552(2-Ethoxy-3-isopropylphenyl)methanol

Product 1

HCID 592775432-Ethoxy-3-isopropylbenzaldehydeYield 42.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

MnO2 (9.49 g, 109 mmol) was added to a stirring solution of (2-ethoxy-3-isopropylphenyl)methanol (3.54 g, 18.2 mmol) in benzene (175 mL) under N2. After stirring for 48 h, the solution was filtered over diatomaceous earth and the pad rinsed with CH2Cl2 (200 mL), and the solution was concentrated to a clear oil. Purification by column chromatography (silica gel, hexanes/EtOAc, 100 to 98:2) gave the title compound (1.49 g, 42%) as a light yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 7.67 (dd, J=7.6, 1.7 Hz, 1H), 7.59 (dd, J=7.6, 1.7 Hz, 1H), 7.28 (t, J=7.6 Hz, 1H), 3.97 (q, J=6.9 Hz, 2H), 3.32-3.30 (m, 1H), 1.39 (t, J=6.9 Hz, 3H), 1.21 (d, J=6.9 Hz, 6H).

Workup

  1. filtrationthe solution was filtered over diatomaceous earth
  2. washthe pad rinsed with CH2Cl2 (200 mL)
  3. concentrationthe solution was concentrated to a clear oil
  4. customPurification by column chromatography (silica gel, hexanes/EtOAc, 100 to 98:2)

Sources & evidence

ORD record
ord-49bbf79ad6314374adcd8632e8412280
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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