Lithium Hydroxide → 6-(Tert-butoxy)-6-oxohexanoic acid

HRID 63401Notes

Reaction equation

HRID 63401 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:17])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>CO.O>[C:13]([O:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:17])=[O:4])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 184750351-(1,1-Dimethylethyl) 6-methyl hexanedioate

Product 1

HCID 159089376-(Tert-butoxy)-6-oxohexanoic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Lithium hydroxide (0.53 g, 22 mmol) was added to a solution of hexanedioic acid tert-butyl ester methyl ester (4.8 g, 22 mmol) in 3:1 methanol-water (80 mL), and the resulting mixture was stirred at room temperature for 16 hours. The mixture was evaporated under vacuum. The residue was partitioned between water (60 mL) and methylene chloride (75 mL), and the aqueous phase was washed with methylene chloride (3×75 mL) and evaporated, providing 4.0 g of hexanedioic acid mono-tert-butyl ester, lithium salt; 1H NMR (D2O) δ 1.45 (s, 9H), 1.54-1.58 (m, 4H), 2.15-2.20 (m, 2H), 2.25-2.34 (m, 2H).

Workup

  1. customThe mixture was evaporated under vacuum
  2. customThe residue was partitioned between water (60 mL) and methylene chloride (75 mL)
  3. washthe aqueous phase was washed with methylene chloride (3×75 mL)
  4. customevaporated

Sources & evidence

ORD record
ord-26bfa110666f4cc095549042b2167b1e
Source dataset
uspto-grants-2016_09
Patent number
US09447070B2

Reaction notes

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