Water → HCID 20262667, compound

HRID 464800Notes

Reaction equation

HRID 464800 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH2:5][C:6]([CH3:8])=[CH2:7])[CH:3]=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:1][C:2]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([CH2:5][C:6]([CH3:8])=[CH2:7])[CH2:3][OH:4]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 13529609HCID 13529609, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20262667HCID 20262667, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

A 376 g sample of 2,4-dimethyl-2-phenyl-4-pentenal (prepared via the method of U.S. Pat. No. 3,996,290) was added to 38 g of lithium aluminum hydride in 1200 ml of anhydrous ether over a 1 hr period with cooling to maintain 25° C. At the end of the addition, 76 g of water and 61 g of 10% aqueous sodium hydroxide were carefully added and the mixture was stirred for 2 hrs. The mixture was filtered, concentrated on a rotary evaporator and distilled, affording 370 g of 2,4-dimethyl-2-phenyl-4-penten-1-ol, (bp 125°-127°/0.5 mm Hg), in a 97% yield and a purity of 99%. Spectral data were in agreement with the assigned structure.

Workup

  1. temperaturewith cooling
  2. additionwere carefully added
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated on a rotary evaporator
  5. distillationdistilled

Sources & evidence

ORD record
ord-bcf8cb7c1e3141edbff33439164cef59
Source dataset
uspto-grants-1985_10
Patent number
US04549029

Reaction notes

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