Dichloromethane → Naphthalene

HRID 513337Notes

Reaction equation

HRID 513337 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(Cl)Cl>CCOCC>[CH:7]1[C:11]2[C:11](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 178418287HCID 178418287, compound

Product 1

HCID 931NaphthaleneYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a one-neck 50 mL round-bottomed flask equipped with a septum pierced with a needle and a stir bar, was added pyridinium chlorochromate (2.31 g, 10.7 mmol) and DCM (20 mL) with stirring. Alcohol S10 (0.600 g, 5.35 mmol) was added all at once via syringe, and the reaction turned dark brown and thick. The reaction was stirred at rt for 3.5 h until complete by TLC, followed by addition of Et2O (25 mL) and silica gel (10 g). The suspension was stirred for 30 min, filtered through a pad of silica gel with Et2O washings, and then concentrated under reduced pressure to yield the aldehyde xx as a yellow oil (0.478 g, 81%). The crude product was carried on without further purification. Compound S11 was previously characterized.

Workup

  1. customTo a one-neck 50 mL round-bottomed flask equipped with a septum
  2. addition(0.600 g, 5.35 mmol) was added all at once via syringe
  3. stirringThe reaction was stirred at rt for 3.5 h until complete by TLC
  4. stirringThe suspension was stirred for 30 min
  5. filtrationfiltered through a pad of silica gel with Et2O washings
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-611ddb840d2647829f131eff1c89b17d
Source dataset
uspto-grants-2015_08
Patent number
US09102703B2

Reaction notes

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