Water → 2-(1-cyclopropylethoxy)Acetic acid

HRID 1940152Notes

Reaction equation

HRID 1940152 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([OH:7])=[O:6].[CH3:8][CH:9]([CH:11]1[CH2:13][CH2:12]1)[OH:10].O>C1COCC1>[CH:11]1([CH:9]([O:10][CH2:4][C:5]([OH:7])=[O:6])[CH3:8])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 791041-Cyclopropylethanol

Product 1

HCID 221142352-(1-cyclopropylethoxy)Acetic acidYield 29.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of NaH (80% in oil) (15.7 g, 523 mmol) in THF (180 mL) at 0° C. were added bromoacetic acid (28.0 g, 203 mmol) and a-methylcyclopropane methanol (10.0 g, 116 mmol). The resulting mixture was then stirred at 70° C. After a period of 18 h, the reaction mixture was poured over cold H2O and the H2O phase was extracted once with Et2O. The water phase was acidified with HCl and extracted twice with Et2O. The ether was dried over MgSO4, filtered and evaporated under reduced pressure. The crude oil was then purified by flash chromotography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH) to provide 5.0 g of the title compound.

Workup

  1. extractionthe H2O phase was extracted once with Et2O
  2. extractionextracted twice with Et2O
  3. dry with materialThe ether was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude oil was then purified by flash chromotography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH)

Sources & evidence

ORD record
ord-3ff117b57323455d82084b330c75046f
Source dataset
uspto-grants-1997_12
Patent number
US05698584

Reaction notes

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