Hydrochloric Acid → HCID 54439673, compound

HRID 1975633Notes

Reaction equation

HRID 1975633 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8](=[CH:11][CH2:12][CH:13]1[CH2:17][CH2:16][CH:15]([CH3:18])[C:14]1([CH3:20])[CH3:19])[CH:9]=[O:10].[H][H].Cl.[OH-].[Al+3].[OH-].[OH-]>O.C(OCC)C>[CH3:7][C:8](=[CH:11][CH2:12][CH:13]1[CH2:17][CH2:16][CH:15]([CH3:18])[C:14]1([CH3:19])[CH3:20])[CH2:9][OH:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10176082Aluminum HydroxideHCID 21226445Aluminium lithium hydrideHCID 542207162-Methyl-4-(2,2,3-trimethylcyclopent-1-yl)-but-2-enalHCID 178418361HCID 178418361, compound

Product 1

HCID 54439673HCID 54439673, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of 1.5 g (0.04 mole) of lithium aluminium hydride and 75 ml of dried diethyl ether are added over 1/2 hour 15 g (0.08 moles) of 2-methyl-4-(2,2,3-trimethylcyclopent-1-yl)-but-2-enal. The mixture is heated under argon to reflux for 2 hours. It is cooled with ice water and, with caution, treated first with water until hydrogen no longer evolves and then with HCl 5%, whereupon the aluminium hydroxide precipitate dissolves. The material is extracted with ether and the combined organic phases are washed with saturated common salt; it is then dried over MgSO4 and distilled. A fractional vacuum distillation leads to 8.3 g of 2-methyl-4-(2,2,3-trimethyl-cyclopent-1-yl)-but-2-en-1-ol (mixture of isomers) (55% yield);

Workup

  1. temperatureThe mixture is heated under argon
  2. temperatureto reflux for 2 hours
  3. extractionThe material is extracted with ether
  4. washthe combined organic phases are washed with saturated common salt
  5. dry with materialit is then dried over MgSO4
  6. distillationdistilled
  7. distillationA fractional vacuum distillation

Sources & evidence

ORD record
ord-a0c40f6db8cb4c41bcce3ae499928c29
Source dataset
uspto-grants-1994_02
Patent number
US05288701

Reaction notes

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