2-Chloroethanol → HCID 59205673, compound

HRID 908650Notes

Reaction equation

HRID 908650 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].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:25][CH2:26][OH:27]>CN(C=O)C.Cl>[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][CH2:25][CH2:26][OH:27]

Participants

6

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 120841702,6-Dichloro-4-benzyloxyphenol

Product 1

HCID 59205673HCID 59205673, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 13 grams (0.048 mole) of 2,6-dichloro-4-phenylmethoxyphenol (known compound), 6.8 grams (0.048 mole) of potassium carbonate and 3.9 grams (0.048 mole) of 2-chloroethanol in 80 mL of DMF was heated to 70° C. where it stirred for three hours. After this time the reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with 100 mL of aqueous 10% hydrochloric acid then extracted with three 150 mL portions of ethyl acetate. The combined extracts were washed with an aqueous saturated sodium chloride solution, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The crude residue was purified with column chromatography on silica gel using 6:4 heptane:ethyl acetate as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 10.3 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionthen extracted with three 150 mL portions of ethyl acetate
  3. washThe combined extracts were washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residue
  7. customThe crude residue was purified with column chromatography on silica gel using 6:4 heptane
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d25009e8e0814d96a2f9f9719301d74b
Source dataset
uspto-grants-2011_09
Patent number
US08017635B2

Reaction notes

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