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

HRID 370260Notes

Reaction equation

HRID 370260 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(=O)CI(C1C=CC=CC=1)CC(C(F)(F)F)=[O:24].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:24])=[CH:8][C:7]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 86756003HCID 86756003, compound

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(trifluoroacetony)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-0823f6abf9df4175bff4d18bdb3e3efa
Source dataset
uspto-grants-2000_10
Patent number
US06140345

Reaction notes

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