2-Hydroxyethylmesitylene → 2-(2,4,6-Trimethylphenyl)acetaldehyde

HRID 2422010Notes

Reaction equation

HRID 2422010 reaction equation
[C:1]1([CH3:12])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][CH2:10][OH:11].C(OI1(OC(=O)C)(OC(=O)C)C2C=CC=CC=2C(=O)O1)(=O)C>C(Cl)Cl>[C:3]1([CH3:8])[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:12])[C:2]=1[CH2:9][CH:10]=[O:11]

Participants

4

Reactant 2

HCID 813892-HydroxyethylmesityleneHCID 159087Triacetoxyperiodinane

Product 1

HCID 3003822-(2,4,6-Trimethylphenyl)acetaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Mesitylethanol (0.99 g, 6.0 mmol) was dissolved in DCM (10.0 mL, dry) and cooled to 0° C. 1,1,1-Tris(acetyloxy)-1λ5,2-benziodoxol-3(1H)-one (Dess-Martin periodinane) in DCM (15 wt %, 2.80 g, 6.60 mmol) was added dropwise over a period of 20 mins. The ice bath was removed and the reaction mixture was stirred at rt for 4 h. NaOH (2N, 5 mL) was added to the mixture and it was diluted with water (5 mL). The layers were separated and the organic layer was washed with water, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica gel using heptane and EtOAc as eluant giving the title compound (0.69 g, 71%). 1H NMR (CDCl3, 400 MHz) δ 9.68-9.65 (m, 1H), 6.94-6.90 (m, 2H), 3.75-3.71 (m, 2H), 2.29 (s, 3H), 2.27 (s, 6H).

Workup

  1. customThe ice bath was removed
  2. additionNaOH (2N, 5 mL) was added to the mixture and it
  3. additionwas diluted with water (5 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0cb7ad8c9f834f808fcb5986e17eca63
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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