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

HRID 1456820Notes

Reaction equation

HRID 1456820 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 CH2 Cl2. 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 CH2 Cl2
  3. filtrationThe biphasic mixture was filtered
  4. customthe organic phase collected
  5. washwashed with saturated NaHCO3 solution
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d8970dcad3c94c8287c79c6e1c63e7d2
Source dataset
uspto-grants-1998_12
Patent number
US05843977

Reaction notes

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