Lithium hydroxide, monohydrate → HCID 69830595, compound

HRID 1017558Notes

Reaction equation

HRID 1017558 reaction equation
[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:15][C:16]([O:18]C)=[O:17])[CH:12]=[CH:13][CH:14]=2)[CH2:4][O:3]1.O[Li].O>CO.O>[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69830462HCID 69830462, compound

Product 1

HCID 69830595HCID 69830595, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)phenyl-acetate (23 g, 0.08 mol) in methanol (80 mL) and water (5 mL) was added LiOH-H2O (13.8 g, 4 eq.). After stirring the reaction mixture at room temperature for 4 h, the volatiles were removed under vacuo and the residue was partitioned between EtOAc and H20. 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)phenylacetic acid as a white solid (22 g, >99% yield).

Workup

  1. customthe volatiles were removed under vacuo
  2. customthe residue was partitioned between EtOAc and H20
  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-f967a0bb48654f4d8e52b5e200702530
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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