Dimethyl Sulfoxide → 2-Naphthaleneacetaldehyde

HRID 902574Notes

Reaction equation

HRID 902574 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][OH:13].C(Cl)Cl.CS(C)=O.C(N(CC)CC)C>O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH:12]=[O:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 738772-Naphthaleneethanol

Product 1

HCID 108991132-NaphthaleneacetaldehydeYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an amount of 515.8 mg of 2-naphthaleneethanol was added with 30 ml of methylene chloride and dissolved therein, added with 6.3 ml of dimethyl sulfoxide, 2.5 ml of triethylamine, and 1.4 g of sulfur trioxide/pyridine complex, stirred at room temperature for 2 hours, then added with 50 ml of water, and extracted with 50 ml of ethyl acetate, and the organic layer was successively washed with 30 ml of saturated aqueous ammonium chloride, and 30 ml of saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure to obtain 511 mg of 2-(naphthalen-2-yl)acetaldehyde.

Workup

  1. dissolutiondissolved
  2. extractionextracted with 50 ml of ethyl acetate
  3. washthe organic layer was successively washed with 30 ml of saturated aqueous ammonium chloride, and 30 ml of saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e72895012daa44d482a1d78c4a015e5a
Source dataset
uspto-grants-2008_04
Patent number
US07365174B2

Reaction notes

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