Acetic Acid → HCID 54315044, compound

HRID 918329Notes

Reaction equation

HRID 918329 reaction equation
[CH3:1][C:2]([CH:8]=[CH:9][CH2:10][CH:11]([CH3:18])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:3][C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)C>CCOCC>[CH3:1][C:2]([CH:8]=[CH:9][CH2:10][CH:11]([CH3:18])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:3][CH2:4][OH:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 21226445Aluminium lithium hydrideHCID 54459735Methyl 3,7,11-trimethyldodeca-2,4,10-trienoate

Product 1

HCID 54315044HCID 54315044, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2 g. of methyl 3,7,11-trimethyldodeca-2,4,10-trienoate and 20 ml. of dry ether, at -78°, is added slowly about 0.4 g. of lithium aluminum hydride in dry ether. The mixture is allowed to stand about 1 hour after addition is complete and then allowed to warm up to room temperature. Then 2.5 ml. of acetic acid is added. The mixture is then washed with ice water and the organic phase separated, which is dried over magnesium sulfate and evaporated to yield 3,7,11-trimethyldodeca-2,4,10-trien-1-ol.

Workup

  1. additionafter addition
  2. washThe mixture is then washed with ice water
  3. customthe organic phase separated
  4. dry with materialwhich is dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d57a17f1d2fb40a9a3c83b5434ba4200
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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