Hydrochloric Acid → HCID 85817686, compound

HRID 992790Notes

Reaction equation

HRID 992790 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:22])[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH:10]([C:16]2[C:20](=C)[CH:19]=[CH:18][CH:17]=2)[CH2:9]1.[NH4+].[Cl-].Cl>O1CCCC1.O>[CH:16]1([CH:10]2[CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:8]([CH3:22])([CH3:7])[CH2:9]2)[CH:17]=[CH:18][CH:19]=[CH:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23436675HCID 23436675, compound

Product 1

HCID 85817686HCID 85817686, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 500 mL flask was charged with LiAlH4 (2.50 g, 65.9 mmol) and 200 mL tetrahydrofuran. An addition funnel containing 3,3,5,5-tetramethylcyclohexylfulvene (11.89 g, 58.8 mmol) dissolved in 50 mL tetrahydrofuran was attached. The vessel was cooled to 0° C. before dropwise addition over 25 minutes. After 17 hours of stirring at room temperature, the vessel was cooled to 0° C. and 20 mL of water were added dropwise. Then, aqueous NH4Cl (100 mL) and water (200 mL) were added before the organic layer was isolated. 15 mL of concentrated aqueous HCl were added to the aqueous layer and it was extracted with diethyl ether (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and rotavapped to provide 11.87 grams of product (98.8%) as a light orange oil. MS (GC-MS) m/z 204.3 (M+).

Workup

  1. temperaturethe vessel was cooled to 0° C.
  2. customwas isolated
  3. extractionwas extracted with diethyl ether (3×50 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2d8f07a9b4e7482a9830176e0059c179
Source dataset
uspto-grants-2002_10
Patent number
US06469188B1

Reaction notes

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