Water → 11-Methoxy-3,7,11-trimethyldodeca-2,4-dien-1-ol

HRID 918333Notes

Reaction equation

HRID 918333 reaction equation
[CH3:1][O:2][C:3]([CH3:21])([CH3:20])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:19])[CH2:8][CH:9]=[CH:10][C:11]([CH3:18])=[CH:12][C:13](OCC)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:1][O:2][C:3]([CH3:20])([CH3:21])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:19])[CH2:8][CH:9]=[CH:10][C:11]([CH3:18])=[CH:12][CH2:13][OH:14]

Participants

6

Reactant 4

HCID 962Water3×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53639252Ethyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

Product 1

HCID 5428054911-Methoxy-3,7,11-trimethyldodeca-2,4-dien-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 6.2 g. of ethyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate in 80 ml. of dry ether is added 3.2 ml. of lithium aluminum hydride (3.9M) in ether slowly, at -78°, with stirring, under argon. The mixture is stirred for 2 hours at -78° and then warmed to about -50°. After 1 hour, the mixture is warmed slowly to about -10° over 4 hours. Then there is added 0.5 ml. of water, 0.5 ml. of 15% sodium hydroxide and 1.5 ml. of water. The mixture is then poured into water, washed with water and brine, dried over magnesium sulfate and evaporated to yield 11-methoxy-3,7,11-trimethyldodeca-2,4-dien-1-ol.

Workup

  1. temperaturewarmed to about -50°
  2. waitAfter 1 hour
  3. temperaturethe mixture is warmed slowly to about -10° over 4 hours
  4. additionThen there is added 0.5 ml
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-428c972adbc34f6482e03ad1911936a1
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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