Lithium Hydroxide → HCID 69830942, compound

HRID 1017595Notes

Reaction equation

HRID 1017595 reaction equation
[CH3:1][C:2]1([CH3:22])[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:10]([N+:19]([O-:21])=[O:20])=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14]C)=[O:13])[CH2:4][O:3]1.[OH-].[Li+]>CO.O>[CH3:1][C:2]1([CH3:22])[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:10]([N+:19]([O-:21])=[O:20])=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69830047HCID 69830047, compound

Product 1

HCID 69830942HCID 69830942, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)-2-nitrobenzoate (2.8 g, 9 mmol) was dissolved in 25 mL of methanol and 2 mL of water. To the above solution was added lithium hydroxide (1.13 g, 3 eq.). After stirring the reaction mixture at room temperature for 5 h, the volatile was removed under vacuo and the residue was partitioned between EtOAc and H2O. The aqueous layer was separated, cooled with an ice bath, and then acidified with 10% aq. HCl. The acidic aqueous layer was extracted with EtOAc. The EtOAc layer was washed with NaCl (sat.), dried over Na2SO4, and concentrated to give 3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)-2-nitrobenzoic acid as a white solid (1.9 g).

Workup

  1. customthe volatile was removed under vacuo
  2. customthe residue was partitioned between EtOAc and H2O
  3. customThe aqueous layer was separated
  4. temperaturecooled with an ice bath
  5. extractionThe acidic aqueous layer was extracted with EtOAc
  6. washThe EtOAc layer was washed with NaCl (sat.)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-321f76f236264b5692f90e0c414359e1
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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