Hydrochloric Acid → (3,5-Dimethoxyphenyl) (tetrahydropyran-4-yl)methanol

HRID 1027366Notes

Reaction equation

HRID 1027366 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[O:8])[CH2:3][CH2:2]1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([Mg]Cl)[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1.Cl>O1CCCC1>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[OH:8])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 178493478HCID 178493478, compound

Product 1

HCID 58079349(3,5-Dimethoxyphenyl) (tetrahydropyran-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrahydropyran-4-carboxaldehyde (16.0 g, 0.14 mol) in tetrahydrofuran (60 ml) is added dropwise over 1 hour to a 1 M solution of 3,5-dimethoxyphenylmagnesium chloride in tetrahydrofuran (140 ml), maintaining the reaction at or below reflux by external cooling. Once the addition is complete, and the exotherm has subsided, the reaction mixture is allowed to stir at room temperature overnight. A solution of dilute aqueous hydrochloric acid (300 ml) is added carefully and the reaction mixture is extracted with ethyl acetate. The organic extract is dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated in vacuo. Purification by column chromatography on silica gel gives (3,5-dimethoxyphenyl) (tetrahydropyran-4-yl)methanol as a cream solid.

Workup

  1. temperaturemaintaining
  2. customthe reaction at or
  3. temperaturebelow reflux by external cooling
  4. additionOnce the addition
  5. extractionthe reaction mixture is extracted with ethyl acetate
  6. extractionThe organic extract
  7. dry with materialis dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo
  10. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-cc73f9a82869442b9542810b2b680c52
Source dataset
uspto-grants-2014_05
Patent number
US08735322B2

Reaction notes

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