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

HRID 331540

Reaction equation

HRID 331540 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-0c8b0c57370c4c28afc7cb9d2a04bc14
Source dataset
uspto-grants-2014_11
Patent number
US08877780B2

Linked notes

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