Potassium Persulfate → HCID 15221418, compound

HRID 986557Notes

Reaction equation

HRID 986557 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:16].[K+].[K+]>C(#N)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH:1]([C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1)=[O:16]

Participants

6

Reactant 2

HCID 24412Potassium PersulfateHCID 347932methyl 3-(4-methylphenoxy)propanoate

Product 1

HCID 15221418HCID 15221418, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 3-(4-methylphenoxy)-propanoate, (15.0 g, 0.077 moles) in acetonitrile, (270 ml), was added to a solution of potassium peroxydisulphate, (41.60 g, 0.154 moles) and copper (II) sulphate (3.85 g, 0.015 moles) in water, (270 ml). The resulting mixture was stirred at 65°-70° C. for 3.5 h, then cooled and extracted with diethyl ether. The organic extract was washed with water, saturated brine and dried, (MgSO4). Evaporation of the solvent gave 14.83 g of an orange oil which was distilled at 0.1 mm/Hg to yield 7.40 g (47%) of the title compound as an oil which crystallized, mp 48°-50° C., υmax (mull) 1735, 1680, (shoulder at 1685), 1605, 1580, 1515 cm-1 δ(CDCl3) 2.81 (2H, t, J 6 Hz, CH2CO2) 3.72 (3H, S, CH3) 4.30 (2H, t, J6 Hz OCH2) 7.39 (4H, ABq, Δυ75 Hz, J9 Hz C6H4) 9.90 (1H, s, CHO).

Workup

  1. temperaturecooled
  2. extractionextracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with water, saturated brine
  5. customdried
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-eca228ccf71e44f684f603f29f609b19
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

Loading…