HCID 19763616, compound → HCID 19763623, compound

HRID 248417Notes

Reaction equation

HRID 248417 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:15][Cl:16])[CH2:13][CH:12]([OH:14])[CH2:11][O:10]1>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:15][Cl:16])[CH2:13][C:12](=[O:14])[CH2:11][O:10]1

Participants

3

Reactant 1

HCID 19763616HCID 19763616, compound

Product 1

HCID 19763623HCID 19763623, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The oily residue obtained in stage a) is then heated in toluene (100 cc) and butanol (200 cc) in the presence of paratoluenesulphonic acid (0.5 g), with the separation of the water formed. After evaporating the reaction medium, the residue is chromatographed on a silica column (40:60 ethyl acetate/heptane eluant) to obtain a colourless oil (14.5 g) corresponding to a mixture of alcohol diastereoisomers, namely 2-(2,4-dichlorophenyl)-4-hydroxy-2-chloromethyltetrahydrofuran. This product is directly oxidized with chromic anhydride in acetic acid to obtain, after purification by silica column chromatography, furanone in the form of white crystals, m.p. 99° C.

Workup

  1. customto obtain
  2. customafter purification by silica column chromatography, furanone in the form of white crystals, m.p. 99° C.

Sources & evidence

ORD record
ord-93769233ea1a4b3db2046687f2096af4
Source dataset
uspto-grants-1993_05
Patent number
US05210198

Reaction notes

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