Hydrochloric Acid → HCID 118795, compound

HRID 2057726Notes

Reaction equation

HRID 2057726 reaction equation
[Mg].O1CCCC1.CO[CH:9]([O:19]C)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Cl.Cl.[C:22]1(C)[CH:27]=[CH:26]C=[CH:24][CH:23]=1>C(Cl)CCC>[CH:9](=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:24][CH:23]=[CH:22][CH2:27][CH3:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 8028TetrahydrofuranHCID 5462224MagnesiumHCID 20330119HCID 20330119, compound

Product 1

HCID 118795HCID 118795, compound

Reagents, catalysts & solvents 1

HCID 8005Butyl ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

To 0.85 gm of magnesium in a thoroughly dried flask equipped with condensor and magnetic stirrer was added 5 mls of anhydrous tetrahydrofuran and 1.06 mls of butyl chloride and 5 mls of dry toluene. This mixture was heated with stirring at 70° C. for about two hours. A solution of 4.44 gms of 1,1-dimethoxy-9-chloro nonane in 50 mls of toluene was added all at once. The temperature was maintained at 75°±5° for one and one quarter hours. The Grignard reagent was decanted into another flask and 3.12 gms of a mixture (approximately 60:40) of 1-chloro-2-pentene and 3-chloro-1-pentene was added. The reaction was maintained at 75°±5° with stirring. The reaction mixture became cloudy within one-half to three-quarters of an hour indicating the initiation of the coupling reaction. This was confirmed by GLC of a hydrolysed aliquot of reaction mixture. The reaction was allowed to continue until a test for Grignard reagent was negative (approximately 2 hours). 50 mls of 3 N hydrochloric acid was then added, the reaction mixture was then stirred and heated at reflux for 1 hour. The aqueous layer was separated, washed two times with toluene. The organic layer and the toluene washes were combined and dried over sodium sulphate. The solvents were removed on the rotary evaporator and the residue was distilled. The majority of the material distilled at 95° at 0.35 torr yielding 2.48 gms of crude 11-tetradecenal. For physical constants see Example 5.

Workup

  1. temperatureThis mixture was heated
  2. temperatureThe temperature was maintained at 75°±5° for one and one quarter hours
  3. customThe Grignard reagent was decanted into another flask
  4. addition3.12 gms of a mixture (approximately 60:40) of 1-chloro-2-pentene and 3-chloro-1-pentene was added
  5. temperatureThe reaction was maintained at 75°±5°
  6. stirringwith stirring
  7. customto three-quarters of an hour
  8. customthe initiation of the coupling reaction
  9. customThis was confirmed by GLC of a hydrolysed aliquot of reaction mixture
  10. custom(approximately 2 hours)
  11. stirringthe reaction mixture was then stirred
  12. temperatureheated
  13. temperatureat reflux for 1 hour
  14. customThe aqueous layer was separated
  15. washwashed two times with toluene
  16. dry with materialdried over sodium sulphate
  17. customThe solvents were removed on the rotary evaporator
  18. distillationthe residue was distilled
  19. distillationThe majority of the material distilled at 95° at 0.35 torr

Sources & evidence

ORD record
ord-564c55e2dce8421ebf8e84b517f7f46e
Source dataset
uspto-grants-1980_07
Patent number
US04212830

Reaction notes

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