Dimethyl Sulfide → HCID 21515720, compound

HRID 1284180Notes

Reaction equation

HRID 1284180 reaction equation
CSC.ClN1C(=O)CCC1=O.[CH:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])([CH3:14])[CH3:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[O:22])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 20136779HCID 20136779, compound

Product 1

HCID 21515720HCID 21515720, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

7.5 cc (0.132 mol) of dimethyl sulphide are added dropwise at 0°, whilst stirring and under nitrogen, to a solution of 13.4 g (0.10 mol) of N-chlorosuccinimide in 250 cc of absolute toluene. A white precipitate is formed. The reaction mixture is subsequently cooled to -25° and a solution of 8.0 g (0.05 mol) of 6-isopropoxyhexanol in 25 cc of absolute toluene is added over the course of 15 minutes. After stirring at -25° for 90 minutes, a solution of 7.5 g (0.074 mol) of triethylamine in 25 cc of toluene is added over the course of 15 minutes to the white suspension. The cooling bath is then separated and after 10 minutes 500 cc of ether are added. The organic phase is washed with 1% aqueous hydrochloric acid, water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated at 30° /20 mm Hg. After fractional distillation almost pure 6-isopropoxyhexanol is obtained (B.P. 90-93° /15 mm Hg). Said compound may be used for the production of 1-(7-isopropoxy-1-heptenyl)-4 -nitrobenzene without further purification.

Workup

  1. customA white precipitate is formed
  2. temperatureThe reaction mixture is subsequently cooled to -25°
  3. customThe cooling bath is then separated and after 10 minutes 500 cc of ether
  4. additionare added
  5. washThe organic phase is washed with 1% aqueous hydrochloric acid, water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated at 30° /20 mm Hg
  8. distillationAfter fractional distillation almost pure 6-isopropoxyhexanol
  9. customis obtained (B.P. 90-93° /15 mm Hg)
  10. custommay be used for the production of 1-(7-isopropoxy-1-heptenyl)-4 -nitrobenzene without further purification

Sources & evidence

ORD record
ord-d700a9ded5cf4f2885cf82e8077e4ae4
Source dataset
uspto-grants-1976_08
Patent number
US03978097

Reaction notes

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