Acetic Acid → 4-(Benzyloxy)-3-(tert-butyl)benzaldehyde

HRID 19780Notes

Reaction equation

HRID 19780 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[C:16]([CH3:19])([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:22])C>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:22])=[CH:11][C:10]=1[C:16]([CH3:19])([CH3:18])[CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 508863431-Benzyloxy-2-tert-butyl-4-methyl-benzene

Product 1

HCID 147726344-(Benzyloxy)-3-(tert-butyl)benzaldehyde

Procedure

A solution of 6.985 g 1-benzyloxy-2-tert-butyl-4-methyl-benzene (27 mmol) and 115 g ammoniumcer (IV)-nitrate in 1000 ml acetic acid (50% v/v) was stirred at 90° C. for one hour. After cooling down to RT, the reaction mixture was extracted with AcOEt/heptane 1:9, dried over magnesium sulfate, filtered off and concentrated under vacuo. The residue was purified by flash column chromatography (heptane/AcOEt 95/5 to 90/10) to give 3.48 g of an orange solid. MS (ISP) 269.3 (M+H)+.

Workup

  1. extractionthe reaction mixture was extracted with AcOEt/heptane 1:9
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered off
  4. concentrationconcentrated under vacuo
  5. customThe residue was purified by flash column chromatography (heptane/AcOEt 95/5 to 90/10)

Sources & evidence

ORD record
ord-ba32652dd21c4f8c82cf31c059f4cbec
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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