Isopropyl iodide → HCID 21427681, compound

HRID 437994Notes

Reaction equation

HRID 437994 reaction equation
CC[O-].[Na+].[CH3:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][CH:7]1[SH:13].[CH:14](I)([CH3:16])[CH3:15]>C(O)C>[CH:14]([S:13][CH:7]1[CH2:8][CH:9]([CH3:12])[CH2:10][CH2:11][CH:6]1[CH3:5])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 2723922Sodium ethoxideHCID 21427674HCID 21427674, compound

Product 1

HCID 21427681HCID 21427681, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of N NaOEt in ethanol (50 ml.), was added dropwise to a stirred solution of 2,5-dimethylcyclohexyl mercaptan (4.5 g.) and isopropyl iodide (6 g.) in ethanol (15 ml.). The mixture was stirred at room temperature for 3 hours and refluxed for 1 hour. The ethanol was removed in a rotary evaporator and 2N HCl added to the residue. This was extracted twice with ether and the combined extracts dried (MgSO4). Removal of the ether left a yellow oil (6 g.) which g.l.c. indicated to be almost pure 2,5-dimethylcyclohexyl isopropyl sulphide.

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe ethanol was removed in a rotary evaporator and 2N HCl
  3. additionadded to the residue
  4. extractionThis was extracted twice with ether
  5. dry with materialthe combined extracts dried (MgSO4)
  6. customRemoval of the ether
  7. waitleft a yellow oil (6 g.) which g.l.c

Sources & evidence

ORD record
ord-affc8df224394caeb3c2db1b55488b17
Source dataset
uspto-grants-1977_06
Patent number
US04032661

Reaction notes

Loading…