Potassium Carbonate → 4-[2,6-Dichloro-4-(phenylmethoxy)phenoxy]butan-1-ol

HRID 1611455Notes

Reaction equation

HRID 1611455 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[OH:17].Cl[CH2:19][CH2:20][CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[O:17][CH2:19][CH2:20][CH2:21][CH2:22][OH:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135694-Chloro-1-butanolHCID 120841702,6-Dichloro-4-benzyloxyphenol

Product 1

HCID 222571354-[2,6-Dichloro-4-(phenylmethoxy)phenoxy]butan-1-olYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 33.9 grams (0.126 mole) of 2,6-dichloro-4-phenylmethoxyphenol (known compound), 16.4 grams (0.151 mole) of 4-chlorobutan-1-ol and 20.9 grams (0.151 mole) of potassium carbonate in 300 mL of DMF was warmed to 80° C. where it stirred during an 18 hour period. After this time the reaction mixture was concentrated under reduced pressure to a residue. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with water and then with an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using a mixture of 1:1 ethyl acetate and hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 12.2 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure to a residue
  8. customThe residue was purified with column chromatography on silica gel using
  9. additiona mixture of 1:1 ethyl acetate and hexane as an eluant
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-75e9e94a3a264e08823aca2052e1f6da
Source dataset
uspto-grants-2006_01
Patent number
US06987194B2

Reaction notes

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