Lithium Hydroxide → HCID 58154509, compound

HRID 2359391Notes

Reaction equation

HRID 2359391 reaction equation
[CH3:1][C:2]1([CH3:19])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14]C)=[O:13])[CH2:4][O:3]1.[Li+].[OH-]>C1COCC1.O>[CH3:1][C:2]1([CH3:19])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[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 58154779HCID 58154779, compound

Product 1

HCID 58154509HCID 58154509, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (R)-methyl 3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoate (8.5 g, 32 mmol) in THF (80 ml) was added a solution of LiOH (2.3 g, 96 mmol) in water (20 ml). The mixture was stirred for 15 hours at 40° C. The mixture was concentrated and diluted with saturated solution of Na2CO3 (50 ml), washed with ethyl acetate (50 ml×2), The aqueous layer was adjusted to pH=4 by addition of aqueous 3N HCl. The precipitate was collected by filtration and the filtered cake was dried in vacuo to obtain (R)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoic acid as a white solid, (5.8 g, 72% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with saturated solution of Na2CO3 (50 ml)
  3. washwashed with ethyl acetate (50 ml×2)
  4. additionThe aqueous layer was adjusted to pH=4 by addition of aqueous 3N HCl
  5. filtrationThe precipitate was collected by filtration
  6. customthe filtered cake was dried in vacuo

Sources & evidence

ORD record
ord-d97787dfec3744b1ba16bb9993f595f2
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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