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

HRID 1533421Notes

Reaction equation

HRID 1533421 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-e6c2c048396d43ff998171d3ac65d1bc
Source dataset
uspto-grants-2001_03
Patent number
US06207680B1

Reaction notes

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