Sodium Hydroxide → HCID 67114764, compound

HRID 1844241Notes

Reaction equation

HRID 1844241 reaction equation
[OH-].[Na+].[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:15][C@H:14]2[C:16]([O:18]CC)=[O:17])=[CH:9][CH:8]=1)[CH:4]=[CH2:5]>CO.C1COCC1>[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:15][C@H:14]2[C:16]([OH:18])=[O:17])=[CH:9][CH:8]=1)[CH:4]=[CH2:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 123228626HCID 123228626, compound2×

Product 1

HCID 67114764HCID 67114764, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaOH (6 N aqueous solution, 10 mL) was added to a solution of (trans)-ethyl 2-(4-(allyloxy)phenyl)cyclopropanecarboxylate (Intermediate F, 11.15 g, 45.27 mmol) in methanol (30 mL) and THF (25 mL) and stirred at room temperature for 18 h. After removal of the solvent, the residue was dissolved in CH2Cl2 (200 mL), acidified with HCl (10% aqueous solution, 30 mL), and washed with brine (2×200 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. Removal of the solvent afforded 9.13 of (trans)-2-[4-(allyloxy)phenyl]cyclopropanecarboxylic acid [Rf=0.25 (5% MeOH/CH2Cl2), white solid, 92% yield]

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in CH2Cl2 (200 mL)
  3. washwashed with brine (2×200 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-bf9604b34e124a0b8c33704c8f499176
Source dataset
uspto-grants-2015_02
Patent number
US08946296B2

Reaction notes

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