Acetone → HCID 19764568, compound

HRID 248068Notes

Reaction equation

HRID 248068 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].BrCC(O[C:24]([CH3:27])([CH3:26])[CH3:25])=O.[CH3:28]C(C)=O>[I-].[K+]>[C:24]([CH2:27][C:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)=[O:16])([CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 19764568HCID 19764568, compound

Reagents, catalysts & solvents 1

HCID 4875Potassium IodideCatalyst

Procedure

Dissolve methyl 4-hydroxyphenylacetate (15 g, 90.3 mmol) in acetone (300 mL). Add potassium carbonate (13.7 g, 99.3 mmol), potassium iodide (1.47 g, 9.03 mmol) and t-butyl bromoacetate (16 mL, 99.3 mmol). Heat at reflux for 20 hours then remove 200 mL of acetone in vacuo. Dilute the residue with ethyl ether (500 mL), wash with water (2×300 mL) and brine (300 mL). Dry (MgSO4) and evaporate the solvent in vacuo. Purify by flash chromatography (30→50% ethyl acetate/hexane) to give the title compound (25.79 g).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 20 hours
  3. customthen remove 200 mL of acetone in vacuo
  4. additionDilute the residue with ethyl ether (500 mL)
  5. washwash with water (2×300 mL) and brine (300 mL)
  6. dry with materialDry (MgSO4)
  7. customevaporate the solvent in vacuo
  8. customPurify by flash chromatography (30→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-30f43a615ff44d289caf721fffc9058b
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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