Hydrochloric Acid → 3-Cyclohexen-1-ol, 4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-

HRID 703618Notes

Reaction equation

HRID 703618 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[C:11]([C:16]#[C:17][CH:18]([OH:20])[CH3:19])=[C:10]([CH3:21])[CH2:9]1.O.Cl>COCCOCCOC.O1CCCC1>[OH:7][CH:8]1[CH2:13][C:12]([CH3:14])([CH3:15])[C:11]([CH:16]=[CH:17][CH:18]([OH:20])[CH3:19])=[C:10]([CH3:21])[CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 30155414-(3-Hydroxybutyn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-olHCID 21226445Aluminium lithium hydride

Product 1

HCID 5289693-Cyclohexen-1-ol, 4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-Yield 55.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8150DiglymeSolvent

Procedure

To a suspension of 1.1 g of lithium aluminum hydride in 30 ml of anhydrous diglyme and 10 ml of anhydrous tetrahydrofuran (hereinafter "THF") was added dropwise 10 ml of an anhydrous THF solution containing 5 g of 4-(4-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-yn-2-ol in a nitrogen atmosphere, and the mixture was stirred at reflux for 15 hours. After completion of the reaction, the reaction mixture was cooled and carefully hydrolyzed with water under ice-cooling. The aqueous phase was neutralized with diluted hydrochloric acid and extracted with diethyl ether. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent, etc. were removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2.8 g (yield: 55%) of 4-(4-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en- 2-ol.

Workup

  1. temperatureat reflux for 15 hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled
  4. temperaturecooling
  5. extractionextracted with diethyl ether
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent, etc. were removed by distillation under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-19887e85457a48fc8150c6d9b799c8ea
Source dataset
uspto-grants-1991_01
Patent number
US04983723

Reaction notes

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