Water → 4-(3-Chloropropoxy)-3-methoxyphenyl-2-hydroxyethanone

HRID 55710

Reaction equation

HRID 55710 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:7]=1[O:15][CH3:16].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=[O:20].O.C(C(O)=O)(F)(F)F>CC#N>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH2:13][OH:20])=[CH:8][C:7]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenone

Product 1

HCID 184673324-(3-Chloropropoxy)-3-methoxyphenyl-2-hydroxyethanoneYield 32.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4.3 g, 17.7 mmol), [bis(trifluoroacetoxy)iodo]benzene (15.6 g, 36.2 mmol), H2O (18 ml), CF3CO2H (2.8 ml) and CH3CN (90 ml) was refluxed for 3 hours. The CH3CN was removed under reduced pressure and the resulting yellow liquid was partitioned between H2O and CH2Cl2. The biphasic mixture was filtered, the organic phase collected, washed with saturated NaHCO3 solution and concentrated to afford 1.5 g of an amorphous brown solid. The solid was flash chromatographed on silica gel, eluting the column with 5% EtOAc/CH2Cl2. Concentration of similar fractions afforded 0.7 g of the compound as a pale yellow solid, m.p. 99°-101° C.

Workup

  1. customThe CH3CN was removed under reduced pressure
  2. customthe resulting yellow liquid was partitioned between H2O and CH2Cl2
  3. filtrationThe biphasic mixture was filtered
  4. customthe organic phase collected
  5. washwashed with saturated NaHCO3 solution
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ed01edab93f4cd8a458f79cd4647506
Source dataset
uspto-grants-1997_04
Patent number
US05624927

Linked notes

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