Lithium Hydroxide → (2Z)-3-Methylhepta-2,6-dienoic acid

HRID 1664254Notes

Reaction equation

HRID 1664254 reaction equation
[CH3:1]/[C:2](/[CH2:8][CH2:9][CH:10]=[CH2:11])=[CH:3]/[C:4]([O:6]C)=[O:5].[Li+].[OH-]>C1COCC1.O>[CH3:1]/[C:2](/[CH2:8][CH2:9][CH:10]=[CH2:11])=[CH:3]/[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59644092(Z)-Methyl 3-Methylhepta-2,6-dienoate

Product 1

HCID 13947388(2Z)-3-Methylhepta-2,6-dienoic acidYield 56.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the title compound from Example 20 (6.8 g, 32.5 mmol) in THF (150 mL) was treated with 1 N LiOH (100 mL) and water (125 mL) and stirred vigorously for 4 days. The mixture was diluted with water and washed twice with ether. The aqueous phase was taken to pH 1.5 by addition of 2N HCl and extracted three times with ether. The organic extracts were dried and the solvents evaporated to give the title compound (2.57 g, 56%) as a pale yellow oil.

Workup

  1. washwashed twice with ether
  2. additionThe aqueous phase was taken to pH 1.5 by addition of 2N HCl
  3. extractionextracted three times with ether
  4. customThe organic extracts were dried
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-0f964c413f9b4871a8d24b91383d73d9
Source dataset
uspto-grants-2011_10
Patent number
US08039465B2

Reaction notes

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