Lithium Hydroxide → HCID 13708826, compound

HRID 54169Notes

Reaction equation

HRID 54169 reaction equation
[OH-].[Li+].[CH3:3][C:4](=[CH2:13])/[CH:5]=[CH:6]/[CH2:7][C:8]([O:10]CC)=[O:9]>CO.O1CCCC1.O>[CH3:13][C:4](=[CH2:3])/[CH:5]=[CH:6]/[CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 14524662Ethyl trans-4-methyl-2,4-pentadienecarboxylate

Product 1

HCID 13708826HCID 13708826, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2.5 g (0.1 mol) of lithium hydroxide are added at 0° C. to 10 g (0.07 mol) of ethyl trans-4-methyl-2,4-pentadienecarboxylate, dissolved in a solvent mixture of 75 ml of methanol, 17 ml of tetrahydrofuran and 2.5 ml of water, and the mixture is stirred for 20 hours at room temperature. After the mixture has been diluted with 200 ml of water, it is extracted once using diethyl ether, and a pH of 1 is established in the aqueous phase at 0° C. using concentrated hydrochloric acid. The mixture is extracted using diethyl ether, the combined organic phases are washed several times with water and saturated sodium chloride solution, and, after drying and concentrating, 6.1 g (76% of theory) of trans-4-methyl-2,4-pentadienecarboxylic acid are obtained. ##STR208##

Workup

  1. extractionis extracted once using diethyl ether
  2. customis established in the aqueous phase at 0° C.
  3. extractionThe mixture is extracted
  4. washthe combined organic phases are washed several times with water and saturated sodium chloride solution
  5. customafter drying
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-299d8a018f6644f7be2076f3bd417fef
Source dataset
uspto-grants-1997_04
Patent number
US05622916

Reaction notes

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