Dimethyl Sulfide → HCID 11172431, compound

HRID 2198483Notes

Reaction equation

HRID 2198483 reaction equation
ClN1C(=O)CCC1=O.CSC.[CH2:12]([OH:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH3:27].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:12](=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 12017758HCID 12017758, compound

Product 1

HCID 11172431HCID 11172431, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 27.8 g (207.9 mmol) N-chlorosuccinimide and 450 ml of toluene is cooled to -20° to -25° and 20.4 ml of dimethylsulfide (277.3 mmol) is added all at once. The mixture is stirred at -20° for 30 min. A solution of 33 g (138.6 mmol) of (9Z, 11E)-9,11-hexadecadien-1-ol in 10 ml of toluene is added over a period of 20 min. at -15°, with occasional warming to -5°. After addition is complete, the mixture is stirred at -15° for 20 min., then warmed to -5°, and then cooled to -50° as 38.7 ml (277.3 mmol) of triethylamine is added in one portion. The suspension is allowed to warm to 0° and is then quenched with water. The phases are separated and the aqueous layer is extracted with ether (2X). The combined organic phases are washed with 2 N sulfuric acid, water, saturated sodium bicarbonate and brine and dried over sodium sulfate. Purification by chromatography on a column of silica gel, eluting with hexane, then 10% ether/hexane, followed by recrystallization from hexane at -78° yields pure (9Z,11E)-9,11-hexadecadienal.

Workup

  1. temperatureis cooled to -20° to -25°
  2. temperaturewith occasional warming to -5°
  3. additionAfter addition
  4. stirringthe mixture is stirred at -15° for 20 min.
  5. temperaturewarmed to -5°
  6. additionis added in one portion
  7. temperatureto warm to 0°
  8. customis then quenched with water
  9. customThe phases are separated
  10. extractionthe aqueous layer is extracted with ether (2X)
  11. washThe combined organic phases are washed with 2 N sulfuric acid, water, saturated sodium bicarbonate and brine
  12. dry with materialdried over sodium sulfate
  13. customPurification by chromatography on a column of silica gel
  14. washeluting with hexane
  15. custom10% ether/hexane, followed by recrystallization from hexane at -78°

Sources & evidence

ORD record
ord-6875fbe8917b41b180104865e8771150
Source dataset
uspto-grants-1982_11
Patent number
US04357474

Reaction notes

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