Sodium Hydroxide → 1257122-75-0

HRID 709408Notes

Reaction equation

HRID 709408 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]2[CH2:19][C@H:18]2[C:20]([O:22]CC)=[O:21])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C@@H:17]2[CH2:19][C@H:18]2[C:20]([OH:22])=[O:21])=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66714771HCID 66714771, compound2×

Product 1

HCID 518881081257122-75-0Yield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4N NaOH solution (4 L) was added to a solution of (trans)-ethyl 2-(4-(benzyloxy)phenyl)cyclopropanecarboxylate (Intermediate R, 250 g, 0.844 mol) in Methanol (1.2 L) at 0° C. and stirred at RT for 4 h. After completion, the solvent was evaporated, the residue was diluted with water (1 L), acidified with 4 N HCl solution, extracted with EtOAc (2×2 L). Combined organic extracts were washed with water (1 L), brine (1 L), dried over anhydrous Na2SO4, filtered and evaporated to afford (trans)-2-(4-(benzyloxy)phenyl)cyclopropanecarboxylic acid (190 g, 84%) as off white solid. The crude was carried to next step without further purification.

Workup

  1. customAfter completion, the solvent was evaporated
  2. additionthe residue was diluted with water (1 L)
  3. extractionextracted with EtOAc (2×2 L)
  4. washCombined organic extracts were washed with water (1 L), brine (1 L)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-b247bac6b80b4d4fa625db4797e5ebdc
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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