Lithium hydroxide, monohydrate → 4-(3-tert-Butoxycarbonyl-propoxy)-3-methyl-benzoic Acid

HRID 220857

Reaction equation

HRID 220857 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:9]([CH3:24])[CH:8]=1>C1COCC1.O>[C:20]([O:19][C:17]([CH2:16][CH2:15][CH2:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([OH:25])=[O:5])=[CH:8][C:9]=1[CH3:24])=[O:18])([CH3:22])([CH3:23])[CH3:21]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 575554224-(3-tert-Butoxycarbonyl-propoxy)-3-methyl-benzoic Acid Methyl Ester

Product 1

HCID 575552384-(3-tert-Butoxycarbonyl-propoxy)-3-methyl-benzoic AcidYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (137 mg, 3.26 mmol) was added to a solution of 4-(3-tert-butoxycarbonyl-propoxy)-3-methyl-benzoic acid methyl ester from Example E42.2 (414 mg, 1.34 mmol) in THF (10 ml) and water (5 ml). The mixture was stirred for 48 h at room temperature and concentrated in vacuo. The residue was dissolved in chloroform, acidified with 1M HCl then washed with brine, dried and concentrated in vacuo to yield the title compound (275 mg, 70%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. washthen washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4944d1c25b664a4c91094e9100eb9b76
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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