Lithium Hydroxide → trans-2-Phenylcyclopropanecarboxylic acid

HRID 475058

Reaction equation

HRID 475058 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])C.[Li+].[OH-]>CCO>[C:9]1([C@@H:7]2[CH2:8][C@H:6]2[C:4]([OH:5])=[O:3])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 252496Ethyl trans-2-phenylcyclopropanecarboxylate

Product 1

HCID 237413trans-2-Phenylcyclopropanecarboxylic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 33 (153 g, 804.25 mmol, 1.00 equiv) in EtOH (1 L) was added 1M aq. LiOH (1 L), and the resultant solution was stirred at reflux for 1 h. Volatile solvent was removed under reduced pressure and the residue diluted with EtOAc (1.5 L). The organic phase was washed with water (3×1 L) and brine (1×1 L), dried (Na2SO4), filtered and concentrated in vacuo to afford 117.5 g (90%) of trans-2-phenylcyclopropane-1-carboxylic acid (35) as a white solid.

Workup

  1. temperatureat reflux for 1 h
  2. customVolatile solvent was removed under reduced pressure
  3. additionthe residue diluted with EtOAc (1.5 L)
  4. washThe organic phase was washed with water (3×1 L) and brine (1×1 L)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff02facd245d4296b84ab3ed9020f575
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Linked notes

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