(3-Isopropyl-2-propoxyphenyl)methanol → 3-Isopropyl-2-propoxybenzaldehyde

HRID 2097029Notes

Reaction equation

HRID 2097029 reaction equation
[CH:1]([C:4]1[C:5]([O:12][CH2:13][CH2:14][CH3:15])=[C:6]([CH2:10][OH:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]>C1C=CC=CC=1.O=[Mn]=O>[CH:1]([C:4]1[C:5]([O:12][CH2:13][CH2:14][CH3:15])=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH:10]=[O:11])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59277603(3-Isopropyl-2-propoxyphenyl)methanol

Product 1

HCID 592776233-Isopropyl-2-propoxybenzaldehydeYield 54.7%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

MnO2 (6.88 g, 79.2 mmol) was added to a stirring solution of (3-isopropyl-2-propoxyphenyl)methanol (2.75 g, 13.2 mmol) in benzene (130 mL) under N2. After stirring for 48 h, the solution was filtered over diatomaceous earth, the pad rinsed with CH2Cl2 (200 mL) and the solution concentrated to a yellow oil. Purification by column chromatography (silica gel, hexanes/EtOAc, 100 to 98:2) gave the title compound (1.49 g, 54%) 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), 3.87 (t, J=6.4 Hz, 2H), 3.35-3.30 (m, 2H), 1.85-1.78 (m, 2H), 1.21 (t, J=6.9 Hz, 7H), 1.03 (t, J=7.3 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-80b2787469d64294a5816fd117d0b7ca
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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