2,6-DIETHOXYBENZYL ALCOHOL → 2,6-Diethoxybenzaldehyde

HRID 594259Notes

Reaction equation

HRID 594259 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH3:12])[C:5]=1[CH2:13][OH:14])[CH3:2]>C(Cl)(Cl)Cl.O=[Mn]=O>[CH2:11]([O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[C:5]=1[CH:13]=[O:14])[CH3:12]

Participants

4

Reactant 1

HCID 43777052,6-DIETHOXYBENZYL ALCOHOL

Product 1

HCID 198356802,6-Diethoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A solution of commercially available (2,6-diethoxyphenyl)methanol (500 mg; 2.47 mmol) in anh. CHCl3 (10 ml) was treated with MnO2 (3.342 g; 34.60 mmol), and the resulting mixture was heated to 50° C., under nitrogen, for 20 h. After cooling to rt, the resulting reaction mixture was filtered over celite, and the separated solids were washed with DCM. The filtrate was concentrated to dryness under reduced pressure giving 2,6-diethoxybenzaldehyde as a colorless solid. LC-MS (conditions D): tR=0.89 min.; [M+H]+: 194.99 g/mol.

Workup

  1. temperatureAfter cooling to rt
  2. customthe resulting reaction mixture
  3. filtrationwas filtered over celite
  4. washthe separated solids were washed with DCM
  5. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3ba43ea577fd4e51a2e771dd927d3646
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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