4-Chlorobenzyl mercaptan → HCID 54340232, compound

HRID 918004Notes

Reaction equation

HRID 918004 reaction equation
Cl[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][O:7][CH:8]([CH3:10])[CH3:9].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][SH:17])=[CH:14][CH:13]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH:8]([O:7][CH2:6][CH2:5][CH:4]=[CH:3][CH2:2][S:17][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 804094-Chlorobenzyl mercaptanHCID 23665647Potassium tert-butoxideHCID 54043382HCID 54043382, compound

Product 1

HCID 54340232HCID 54340232, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

8.1 g (0.05 mol) of 1-chloro-5-isopropoxy-2-pentene are added dropwise at 20°-25° during the course of 10 minutes and while stirring to a solution of 7.9 g (0.05 mol) of 4-chloro-benzylmercaptan and 5.6 g (0.05 mol) of potassium tert.butoxide in 150 cc of tert.butanol. The solution which is rendered turbid during the addition is stirred at 60° during the course of 1 hour and is then cooled and filtered. The solvent is distilled off at reduced pressure, the residue is dissolved in ether and the ether solution is washed with saturated salt solution. The ether phase is dried with sodium sulphate and then the ether is distilled off and the residue is chromatographed on silica gel with chloroform. The 4-[(5-isopropoxy-2-pentenylthio)-methyl]-chlorobenzol is obtained as colourless oil having a B.P. of 110°-112°/5.10-4 mm. nD20 = 1.5391.

Workup

  1. additionduring the addition
  2. temperatureis then cooled
  3. filtrationfiltered
  4. distillationThe solvent is distilled off at reduced pressure
  5. dissolutionthe residue is dissolved in ether
  6. washthe ether solution is washed with saturated salt solution
  7. dry with materialThe ether phase is dried with sodium sulphate
  8. distillationthe ether is distilled off
  9. customthe residue is chromatographed on silica gel with chloroform

Sources & evidence

ORD record
ord-7cec49dc7f724d01b67c507c17d975bf
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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