Methyl 3-chloro-4-hydroxybenzoate → 3-(3-Chloro-4-hydroxyphenyl)-3-pentanol

HRID 2354265Notes

Reaction equation

HRID 2354265 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>C1COCC1>[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 2

HCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 178420660HCID 178420660, compound

Product 1

HCID 577634983-(3-Chloro-4-hydroxyphenyl)-3-pentanolYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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/THF (442 mL, 442 mmol) at a rate maintaining the temperature below 27° C. The brownish grey reaction is stirred for 72 h. The reaction mixture is cooled in an ice bath and quenched with satd ammonium chloride (1 ml portions) until evolution of ethane subsides. Additional satd NH4Cl solution is added (total of 50 mL) and the mixture is concentrated to remove most of the THF. The residue is added to water and ether, filtered through diatomaceous earth, and partitioned. The organic layer is washed with brine (3×), MgSO4 dried, and concentrated to give the title compound (28.6 g, 99%).

Workup

  1. temperaturemaintaining the temperature below 27° C
  2. customThe brownish grey reaction
  3. temperatureThe reaction mixture is cooled in an ice bath
  4. customquenched with satd ammonium chloride (1 ml portions) until evolution of ethane subsides
  5. additionAdditional satd NH4Cl solution is added (total of 50 mL)
  6. concentrationthe mixture is concentrated
  7. customto remove most of the THF
  8. additionThe residue is added to water and ether
  9. filtrationfiltered through diatomaceous earth
  10. custompartitioned
  11. washThe organic layer is washed with brine (3×), MgSO4
  12. customdried
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-a5e89a4c4c554e20a5f9dfcbb8b14073
Source dataset
uspto-grants-2010_07
Patent number
US07750184B2

Reaction notes

Loading…