Sodium Hydroxide → HCID 13676043, compound

HRID 520412Notes

Reaction equation

HRID 520412 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1([C:6]([O:8]C(C)(C)C)=[O:7])[CH2:5][CH2:4]1.[OH-].[Na+]>C1COCC1.CO.Cl>[OH:1][CH:2]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:3]1([C:6]([OH:8])=[O:7])[CH2:5][CH2:4]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 534785HCID 534785, compound

Product 1

HCID 13676043HCID 13676043, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 1-(hydroxy(phenyl)methyl)cyclopropanecarboxylate (0.56 g, 2.255 mmol) in THF (4 mL) and MeOH (1 mL) was added 10 N sodium hydroxide (3 mL, 30.0 mmol). The reaction mixture was stirred at rt for 12 h. The reaction was diluted with 1 N HCl, extracted with 2×EtOAc, and the combined organic phase was washed with sat. NaCl, dried (anhydrous Na2SO4), filtered and concentrated to yield 1-(hydroxy(phenyl)methyl)cyclopropanecarboxylic acid (0.35 g, 81% yield) as Cap N-11. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.48-7.26 (m, 5H), 4.94 (s, 1H), 1.46 (ddd, J=9.8, 7.0, 4.3 Hz, 1H), 1.38-1.30 (m, 1H), 1.08 (ddd, J=9.5, 7.1, 4.3 Hz, 1H), 0.93-0.84 (m, 1H).

Workup

  1. extractionextracted with 2×EtOAc
  2. washthe combined organic phase was washed with sat. NaCl
  3. dry with materialdried (anhydrous Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e4e18c5af7c45b78ec0ab15e9d7c131
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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