Lithium hydroxide, monohydrate → 4-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic Acid

HRID 220862Notes

Reaction equation

HRID 220862 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:9]([CH3:22])[CH:8]=1>C1COCC1.O>[C:18]([O:17][C:15](/[CH:14]=[CH:13]/[C:10]1[CH:11]=[CH:12][C:7]([C:6]([OH:23])=[O:5])=[CH:8][C:9]=1[CH3:22])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 575553844-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575553374-((E)-2-tert-Butoxycarbonyl-vinyl)-3-methyl-benzoic AcidYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (384 mg, 9.2 mmol) was added to a solution of 4-((E)-2-tert-butoxycarbonyl-vinyl)-3-methyl-benzoic acid methyl ester from Example E30.1 (1.27 g, 4.6 mmol) in THF (50 ml) and water (20 ml). The mixture was stirred for 20 h at room temperature then solvents were removed in vacuo. The residue was dissolved in EtOAc, washed with 1M KHSO4, water then brine, dried and concentrated in vacuo to yield the title compound (1.1 g, 92%).

Workup

  1. customsolvents were removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 1M KHSO4, water
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-448e9afca7f04cdf80f5039883741757
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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