Lithium Hydroxide → 2,2-Dimethylnon-8-enoic acid

HRID 1669571Notes

Reaction equation

HRID 1669571 reaction equation
C([O:3][C:4](=[O:15])[C:5]([CH3:14])([CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])C.[Li+].[OH-]>C1COCC1.CO.O>[CH3:13][C:5]([CH3:14])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[C:4]([OH:15])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 59497201Ethyl 2,2-dimethylnon-8-enoate

Product 1

HCID 594971782,2-Dimethylnon-8-enoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 2,2-dimethylnon-8-enoic acid ethyl ester (51, 800 mg, 3.77 mmol) and LiOH (806 mg, 18.9 mmol) in THF/MeOH/water, 1:1:0.5, was heated at 50° C. for 2.5 h. Then, additional LiOH (1.60 g, 10 eq) was added. After 15 h, the reaction mixture was concentrated under reduced pressure. The pH of the residue was adjusted to 3 with HCl 1N, extracted with CH2Cl2, washed with brine, dried (MgSO4), filtered and concentrated to give 650 mg (94%) of the title product (52) as a colorless oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-856380999916494fa686ad0d0f9640fe
Source dataset
uspto-grants-2011_08
Patent number
US07989471B2

Reaction notes

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