Sodium Hydroxide → (+-)-trans4-Methylene-2-phenylcyclopentanoic acid

HRID 2301768Notes

Reaction equation

HRID 2301768 reaction equation
[CH2:1]=[C:2]1[CH2:6][C@@H:5]([C:7]([O:9]C)=[O:8])[C@H:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[OH-].[Na+]>CO>[CH2:1]=[C:2]1[CH2:6][C@@H:5]([C:7]([OH:9])=[O:8])[C@H:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12537224Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans-

Product 1

HCID 18686197(+-)-trans4-Methylene-2-phenylcyclopentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl(+−)-trans-4-methylene-2-phenylcyclopentanoate prepared as in Example 20, Step A (28.4 g, 131 mmol) in methanol (400 mL) was added 5N sodium hydroxide (131 mL, 656 mmol). The reaction was heated at 65° C. for 1 h then cooled and concentrated. The residue was taken up diluted with water, acidified with 2M hydrochloric acid and extracted twice with methylene chloride. The organic layers were each washed with brine, dried over sodium sulfate, combined and concentrated in vacuo to give the crude title acid (27.2 g) which was used directly in Step B.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated
  3. additionThe residue was taken up diluted with water
  4. extractionextracted twice with methylene chloride
  5. washeach washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f069cf9ce1e4c2cb6cc5e6ebbb59a4c
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

Loading…