Dimethyl Sulfide → Geranyl chloride

HRID 249132Notes

Reaction equation

HRID 249132 reaction equation
[Cl:1]N1C(=O)CCC1=O.CSC.[CH3:12]/[C:13](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:14]\[CH2:15]O>ClCCl>[CH3:12]/[C:13](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:14]\[CH2:15][Cl:1]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 637566Geraniol

Product 1

HCID 6372219Geranyl chlorideYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4.75 g (35.6 mmol) of N-chlorosuccinimide in 180 mL of dichloromethane at -35° C. (internal thermometer) under argon was added 3.3 mL (45.4 mmol) of dimethyl sulfide over 10 minutes. The mixture was allowed to warm to 0° C. for 15 minutes then cooled again to -35° C. A solution of 5.0 g (32.4 mmol) of (E)-3,7-dimethyl-2,6-octadien-1-ol (geraniol) in 25 mL of dichloromethane was added dropwise over 10 minutes. After addition, the reaction was allowed to warm gradually to 0° C. over 2 hours. After 1 hour at 0° C., the reaction was quenched with ice-cold water, diluted with 500 mL of hexane, and the organic layer was separated. The hexane extract was washed with water, brine, dried over MgSO4 and evaporated to provide 5.21 g (93%) of title compound in the form of a yellow liquid.

Workup

  1. temperaturethen cooled again to -35° C
  2. additionAfter addition
  3. temperatureto warm gradually to 0° C. over 2 hours
  4. customthe reaction was quenched with ice-cold water
  5. additiondiluted with 500 mL of hexane
  6. customthe organic layer was separated
  7. extractionThe hexane extract
  8. washwas washed with water, brine
  9. dry with materialdried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-c141067d2f0645bd8be0ba010f8179b8
Source dataset
uspto-grants-1993_05
Patent number
US05212164

Reaction notes

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