Hydrochloric Acid → 2-(4-Propylidenecyclohexyl)ethanol

HRID 1106364Notes

Reaction equation

HRID 1106364 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7](=[C:10]1[CH2:15][CH2:14][CH:13]([CH2:16][C:17](OC)=[O:18])[CH2:12][CH2:11]1)[CH2:8][CH3:9].O.Cl>C1COCC1>[CH:7](=[C:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1)[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54378474HCID 54378474, compound

Product 1

HCID 187878562-(4-Propylidenecyclohexyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

25.2 g of lithium aluminium hydride were introduced into 100 ml of THF, and a solution of 54.2 g of methyl (4-propylidenecyclohexyl)acetate in 200 ml of THF was then added dropwise with stirring at such a rate that the reaction boiled gently. The mixture was then refluxed for a further 3 h, cooled to RT and hydrolysed dropwise with 50 ml of water. 18% hydrochloric acid was then added until the precipitate formed had dissolved. Conventional work-up gave 2-(4-propylidenecyclohexyl)ethanol (boiling point 110° C. at 10 mmHg).

Workup

  1. temperatureThe mixture was then refluxed for a further 3 h
  2. customformed
  3. dissolutionhad dissolved

Sources & evidence

ORD record
ord-3e03a5583e6e433bb2d6a62cc91945f4
Source dataset
uspto-grants-2000_05
Patent number
US06056895

Reaction notes

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