Diethyl Ether → 2-[1,3-Dithian-2-yl]-5-nitrobenzaldehyde

HRID 280710Notes

Reaction equation

HRID 280710 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[CH2:9][OH:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>C(Cl)Cl>[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 135302832-[1,3-Dithian-2-yl]-5-nitrobenzyl alcoholHCID 178418287HCID 178418287, compound2×

Product 1

HCID 135302842-[1,3-Dithian-2-yl]-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.47 g (12.8 mmol) of the Compound 3c in methylene chloride (100 mL) was added pyridinium chlorochromate (4.15 g, 19.2 mmol). The mixture was stirred for one hour, an additional pyridinium chlorochromate (2.0 g) was added, and the mixture was stirred 15 hours. Diethyl ether (200 mL) was added to the reaction mixture, and the solvent was decanted and evaporated. The residue was purified by chromatography (silica gel, chloroform) to afford the Compound 3d as light yellow crystals; m.p. 99°-101° C.; IR 1730 cm-1 (C=O); 1H NMR δ1.7-2.3 (m,2H, --CH2CH2CH2 --), 2.8-3.3 (m, 4H,--CH2CH2CH2 --), 6.13(s, 1H, --SCHS--), 7.8-8.7 (m,--3H, ArH), 10.45 (s, 1H,CHO).

Workup

  1. stirringthe mixture was stirred 15 hours
  2. customthe solvent was decanted
  3. customevaporated
  4. customThe residue was purified by chromatography (silica gel, chloroform)

Sources & evidence

ORD record
ord-99d47585a5764194bb543df3f1243001
Source dataset
uspto-grants-1986_05
Patent number
US04590276

Reaction notes

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