(R)-benzyl 4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoate → (R)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoic acid

HRID 1172940Notes

Reaction equation

HRID 1172940 reaction equation
[CH3:1][C:2]1([CH3:25])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([O:15]CC3C=CC=CC=3)=[O:14])=[CH:11][CH:10]=2)[CH2:4][O:3]1>[Pd].CO>[CH3:1][C:2]1([CH3:25])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH2:4][O:3]1

Participants

4

Reactant 1

HCID 59556712(R)-benzyl 4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoate

Product 1

HCID 59556573(R)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoic acidYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 500 mL high-pressure flask was charged with palladium on carbon (0.300 g, 0.282 mmol), then MeOH (200 ml) was added, followed by (R)-benzyl 4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoate (6.17 g, 18.02 mmol). The resulting suspension was allowed to shake under an atmosphere of hydrogen (35 Psi) at ambient temperature for 2 hrs. The mixture was filtered through Celite® and the colorless filtrate was concentrated to afford (R)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoic acid as white solid (4.45 g, 17.64 mmol).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe colorless filtrate was concentrated

Sources & evidence

ORD record
ord-4b5f44e3e012413cb5a7870c2335c09d
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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