Water → 3-(3-Oxocyclobutyl)propanoic acid

HRID 511603

Reaction equation

HRID 511603 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])[CH2:3]1.O.[OH-].[Na+]>CO>[O:1]=[C:2]1[CH2:5][CH:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67775333Ethyl 3-(3-oxocyclobutyl)propanoate

Product 1

HCID 677753573-(3-Oxocyclobutyl)propanoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 3-(3-oxocyclobutyl)propanoate (200 mg, 1.18 mmol) in methanol (4 mL) was treated with water (0.75 mL) and a 2N solution of sodium hydroxide (0.75 mL, 1.41 mmol) and the solution was heated at 55° C. till the starting material was consumed by TLC (25% EA/hept). After 1 h the starting material was found to be consumed. The reaction mixture was cooled to room temperature and concentrated to remove the MeOH. The aqueous phase was diluted with 2 mL H2O and made acidic to pH˜2 with 1N HCl. The solution was saturated with NaCl and extracted with three 10 mL portions of ethyl acetate. The organic phase was dried over Na2SO4, filtered and concentrated to yield the title compound (157 mg, 94%) as a light orange viscous oil that was used as is in the next step: GC purity 63.2% (ret. time, 4.27 min).

Workup

  1. customwas consumed by TLC (25% EA/hept)
  2. customto be consumed
  3. concentrationconcentrated
  4. customto remove the MeOH
  5. additionThe aqueous phase was diluted with 2 mL H2O
  6. extractionextracted with three 10 mL portions of ethyl acetate
  7. dry with materialThe organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d6717f638c6e49a0a652ce62ac9a13fc
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Linked notes

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