[3-Chloro-2-(propan-2-yloxy)phenyl]methanol → 3-Chloro-2-isopropoxybenzaldehyde

HRID 2097015Notes

Reaction equation

HRID 2097015 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH:11]([CH3:13])[CH3:12])=[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][CH:11]([CH3:13])[CH3:12])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 59277613[3-Chloro-2-(propan-2-yloxy)phenyl]methanol

Product 1

HCID 592776023-Chloro-2-isopropoxybenzaldehydeYield 31.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

MnO2 (4.86 g, 56.0 mmol) was added to a stirring solution of (3-chloro-2-isopropoxyphenyl)methanol (1.60 g, 8.00 mmol) in benzene (75 mL), under N2. After stirring for 48 h, the solution was filtered over diatomaceous earth, the pad was rinsed with CH2Cl2 (100 mL), and the solution was concentrated to a yellow oil. Purification by column chromatography (silica gel hexanes/EtOAc, 98:2) gave the title compound (0.50 g, 31%) as a clear oil: 1H NMR (300 MHz, DMSO-d6) δ 10.28 (s, 1H), 7.84 (dd, J=7.8, 1.5 Hz, 1H), 7.72 (dd, J=7.8, 1.5 Hz, 1H), 7.31 (t, J=8.1 Hz, 1H), 4.53-4.48 (m, 1H), 1.32 (d, J=6.0 Hz, 6H).

Workup

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

Sources & evidence

ORD record
ord-a98752dd1215482d81e8a3a0ab2e2581
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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