Dimethyl Sulfoxide → HCID 14742767, compound

HRID 1651242Notes

Reaction equation

HRID 1651242 reaction equation
[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:17][OH:18])[CH2:2][CH2:3][CH3:4].CS(C)=O.C(Cl)(=O)C(Cl)=O>ClCCl>[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH:17]=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 14742765HCID 14742765, compound

Product 1

HCID 14742767HCID 14742767, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 136, 1-butyl-7-methoxy-2-naphthalenemethanol (2.25 g) was oxidized by using the reagent prepared from dimethylsulfoxide (0.54 mL) and oxalyl chloride (0.9 mL) in dry dichloromethane (25 mL). The usual work up gave 2 g of 1-butyl-7-methoxy-2-naphthalenecarboxaldehyde and distillation of a sample on a Kugelrohr apparatus (138°-140° C.; 0.1 mm) furnished the analytical specimen. Anal. Calcd for C16H18O2 : C, 79.31; H, 7.49 Found: C, 79.11; H, 7.49

Workup

  1. customThe usual work up gave
  2. distillation2 g of 1-butyl-7-methoxy-2-naphthalenecarboxaldehyde and distillation of a sample on a Kugelrohr apparatus (138°-140° C.; 0.1 mm)
  3. customfurnished the analytical specimen

Sources & evidence

ORD record
ord-ddecbbe16f6c47fda8897bf2f9bbe944
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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