1-Chloro-4-(chloromethyl)benzene → HCID 13561746, compound

HRID 1253274Notes

Reaction equation

HRID 1253274 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][CH2:5][O:4][C:3]1([OH:13])[CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1.[OH-].[K+].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CS(C)=O.O>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][CH:7]([C:3]2([OH:13])[C:2]([CH3:14])([CH3:1])[CH2:6][CH2:5][O:4]2)[N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14797Potassium HydroxideHCID 13561743HCID 13561743, compound

Product 1

HCID 13561746HCID 13561746, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

10.3 g (0.052 mole) of 3,3-dimethyl-2-hydroxy-2-(1,2,4-triazol-1-yl-methyl)-tetrahydrofuran, 2.9 g (0.052 mole) of potassium hydroxide and 8.4 g (0.052 mole) of 4-chlorobenzyl chloride are stirred in a mixture of 100 ml of dimethylsulphoxide and 6 ml of water at 30° C. for 2 hours. The reaction solution is then poured onto water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and concentrated. After trituration in n-hexane, the residue crystallizes. 6.6 g (39.5% of theory) of 1-(4-chlorophenyl)-2-(3,3-dimethyl-2-hydroxy-tetrahydrofuran-2-yl)-2-(1,2,4-triazol-1-yl)ethane of melting point 98° C. are obtained. ##STR100##

Workup

  1. additionThe reaction solution is then poured onto water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated
  5. customAfter trituration in n-hexane, the residue crystallizes

Sources & evidence

ORD record
ord-45cd08f464d34fbf833e25c371d2317f
Source dataset
uspto-grants-1988_05
Patent number
US04748249

Reaction notes

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