Ethyl Acetate → 4-(11-Methoxycarbonylundecyl)benzoic Acid

HRID 2400308Notes

Reaction equation

HRID 2400308 reaction equation
C([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:9][CH:8]=1)(C)(C)C.[OH-].[Na+].CCOC(C)=O>C1COCC1>[CH3:27][O:26][C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([OH:28])=[O:5])=[CH:12][CH:11]=1)=[O:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 689464964-(11-Methoxycarbonylundecyl)benzoic Acid tert-butyl Ester

Product 1

HCID 689443954-(11-Methoxycarbonylundecyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(11-Methoxycarbonylundecyl)benzoic acid tert-butyl ester (185 mg, 0.47 mmol) was dissolved in THF (2 ml), and 1 N NaOH (0.497 mmol) was added over 1 min. The mixture was stirred for 16 h at rt. AcOEt (50 ml) was added and the solution was washed with 5% AcOH (2×25 ml), dried over MgSO4 and concentrated under vacuum to the product (153 mg).

Workup

  1. washthe solution was washed with 5% AcOH (2×25 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum to the product (153 mg)

Sources & evidence

ORD record
ord-3689fcde891b4a29af87fa9ed51023f3
Source dataset
uspto-grants-2014_08
Patent number
US08796205B2

Reaction notes

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