Tetrahydrofuran → 3-(3-Chloro-4-hydroxyphenyl)-3-pentanol

HRID 2354266Notes

Reaction equation

HRID 2354266 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7]C)=O.[CH2:13]([Mg]Br)[CH3:14].[CH2:17]1COC[CH2:18]1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([OH:7])([CH2:13][CH3:14])[CH2:17][CH3:18])[CH:9]=[CH:10][C:11]=1[OH:12]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 178418443HCID 178418443, compound

Product 1

HCID 577634983-(3-Chloro-4-hydroxyphenyl)-3-pentanolYield 99%

Procedure

To a solution of methyl 3-chloro-4-hydroxybenzoate (25.0 g, 133 mmol) in THF (250 mL) is added dropwise 1.0 M ethylmagnesium bromide in THF (442 mL, 442 mmol) so as to maintain the temperature below 27° C. The resulting brownish grey solution is allowed to stir for 72 h during which time a cream-colored gelatinous precipitate is formed. The reaction mixture is cooled in an ice bath and quenched with 1 mL portions of sat. ammonium chloride solution until evolution of ethane subsides. Additional NH4Cl solution is added (to a total of 50 mL) and the resulting mixture is concentrated to remove most of the THF. The resulting residue is distributed into water and ether and filtered through diatomaceous earth to break the partial emulsion that forms. The organic layer is washed 3 times with sat. NaCl, dried over anhydrous magnesium sulfate and concentrated under vacuum to give the title compound (28.6 g, 99%).

Workup

  1. temperatureto maintain the temperature below 27° C
  2. customis formed
  3. temperatureThe reaction mixture is cooled in an ice bath
  4. customquenched with 1 mL portions of sat. ammonium chloride solution until evolution of ethane subsides
  5. additionAdditional NH4Cl solution is added (to a total of 50 mL) and the resulting mixture
  6. concentrationis concentrated
  7. customto remove most of the THF
  8. filtrationfiltered through diatomaceous earth
  9. washThe organic layer is washed 3 times with sat. NaCl
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-09fa76eeee28481c9d6528f25043d1e1
Source dataset
uspto-grants-2010_07
Patent number
US07750184B2

Reaction notes

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