Beta-Propiolactone → HCID 16776070, compound

HRID 1377914Notes

Reaction equation

HRID 1377914 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[C:20]1(=[O:24])[O:23][CH2:22][CH2:21]1>C1COCC1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:22][CH2:21][C:20]([OH:24])=[O:23])=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 2365Beta-PropiolactoneHCID 71034-HydroxybiphenylHCID 23665647Potassium tert-butoxide

Product 1

HCID 16776070HCID 16776070, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution in THF of 4-phenylphenol (1.86 g, 10.9 mmol) was added potassium tert-butoxide (1.22 g, 10.9 mmol). Neat β-propiolactone (0.68 mL, 10.9 mmol) was added dropwise. The resulting white suspension was stirred overnight at ambient temperature and then was concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3. The organic phase was discarded and the aqueous phase was acidified and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, dried over MgSO4, filtered, and concentrated in vacuo to give 3-(4-phenylphenoxy)propionic acid (0.86 g) as a white solid.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3
  3. extractionextracted twice with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-840f12bec98e44f286675b3b345ddf21
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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