(2-Tert-butoxyphenyl)methanol → 2-tert-Butoxybenzaldehyde

HRID 403114Notes

Reaction equation

HRID 403114 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][OH:13])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[C:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 21060300(2-Tert-butoxyphenyl)methanol

Product 1

HCID 149555262-tert-ButoxybenzaldehydeYield 70%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 7 (3.8 g, 21 mmol) in 250 mL CH2Cl2, MnO2 (11 g, 126 mmol) was added. The reaction mixture was stirred overnight, filtered on Celite® and the solvent was distilled under reduced pressure. The crude product was purified by a silica gel column with 17% EtOAc/83% Hexane as eluents. The product was isolated as pale yellow oil (70% yield). 1H NMR (CDCl3) δ 7.286 (dd, 1H, Ar), 7.195 (ddd, 1H, Ar), 7.063 (d, 1H, Ar), 7.003 (ddd, 1H, Ar), 4.669 (s, 2H, —CH2—), 1.447 (s, 9H, —C(CH3)3). Mass Spec.=203.09 (M+H)++Na+.

Workup

  1. filtrationfiltered on Celite®
  2. distillationthe solvent was distilled under reduced pressure
  3. customThe crude product was purified by a silica gel column with 17% EtOAc/83% Hexane as eluents

Sources & evidence

ORD record
ord-132e8456c18a42d5a308eec9eb6c660a
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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