1-Chloro-4-(chloromethyl)benzene → HCID 54340232, compound

HRID 918011Notes

Reaction equation

HRID 918011 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][CH:7]=[CH:8][CH2:9][SH:10])([CH3:3])[CH3:2].[OH-].[Na+].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>C(O)C>[CH:1]([O:4][CH2:5][CH2:6][CH:7]=[CH:8][CH2:9][S:10][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 54324128HCID 54324128, compound

Product 1

HCID 54340232HCID 54340232, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 8.0 g (0.05 mol) of 5-isopropoxy-2-penten-1-thiol and 2 g (0.05 mol) of sodium hydroxide in 30 cc of ethanol are added dropwise at 50° during the course of 45 minutes to a solution of 8.05 g (0.05 mol) of p-chloro-benzylchloride in 25 cc of ethanol, the temperature not exceeding 55°. After the addition is complete the mixture is heated to 60° during 10 minutes. The reaction mixture is filtered, the ethanol is distilled off and the residue is chromatographed on silica gel with chloroform, whereby 4-[(5-isopropoxy-2-pentenylthio)-methyl]-chlorobenzol is obtained which is identical with the compound produced in accordance with Example 40.

Workup

  1. customexceeding 55°
  2. additionAfter the addition
  3. temperatureis heated to 60° during 10 minutes
  4. filtrationThe reaction mixture is filtered
  5. distillationthe ethanol is distilled off
  6. customthe residue is chromatographed on silica gel with chloroform

Sources & evidence

ORD record
ord-1738c255fd2843c09216187ccb4c39c3
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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