Dimethyl Sulfoxide → 3-(2-Naphthyl)propanal

HRID 743395Notes

Reaction equation

HRID 743395 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][CH2:13][OH:14].CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>C(Cl)Cl>[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][CH:13]=[O:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 112062322-Naphthalenepropanol

Product 1

HCID 101764123-(2-Naphthyl)propanalYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Then, following a procedure similar to that described in the second part of Preparation 4, the whole of this 3-(2-naphthyl)propanol was reacted with 2.06 g of dimethyl sulfoxide, 3.35 g of oxalyl chloride and 7.34 ml of triethylamine in 45 ml of methylene chloride. The reaction mixture was worked up and purified as described in the second part of Preparation 4, to give 1.74 g (yield 53%) of 3-(2-naphthyl)propanal as a colorless oil.

Workup

  1. customthat described in the second part of Preparation 4
  2. custompurified
  3. customas described in the second part of Preparation 4

Sources & evidence

ORD record
ord-6523317df26d4fbd950e304391e5a33e
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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