Hydrochloric Acid → HCID 42625427, compound

HRID 2236661Notes

Reaction equation

HRID 2236661 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][Li].Cl>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]([OH:13])[CH3:19])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 42625427HCID 42625427, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-benzyloxy-4-methoxybenzaldehyde (33 mmol maximum) in tetrahydrofuran (150 mL) is cooled to −78° C. Methyllithium (Aldrich, 1.6 M solution in diethyl ether, 31 mL, 49 mmol) is added dropwise via syringe. Following completion of the addition, the cooling bath is removed and the reaction mixture is allowed to warm to room temperature. After 90 minutes at that temperature, the mixture is cooled to 0° C. and quenched by the addition of saturated aqueous sodium hydrogen carbonate. The quenched reaction mixture, after warming to room temperature, is acidified with 1 M hydrochloric acid solution to pH 1 and extracted thrice with diethyl ether. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 1-(3-benzyloxy-4-methoxy-phenyl)-ethanol.

Workup

  1. additioncompletion of the addition
  2. customthe cooling bath is removed
  3. temperaturethe mixture is cooled to 0° C.
  4. customquenched by the addition of saturated aqueous sodium hydrogen carbonate
  5. customThe quenched reaction mixture
  6. temperatureafter warming to room temperature
  7. extractionextracted thrice with diethyl ether
  8. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad86f9ae22154d37b688ff3314fd19ff
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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