4-(Benzyloxy)-3-methoxybenzaldehyde → HCID 11067615, compound

HRID 1636076Notes

Reaction equation

HRID 1636076 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([Mg]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]([OH:14])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 178418336HCID 178418336, compound

Product 1

HCID 11067615HCID 11067615, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20 g (82.64 mmol) of O-benzylvanillin in 200 mL of dry tetrahydrofuran was slowly added to a stirred solution of benzyl magnesium chloride (103.30 mmol) in 150 mL of diethylether at 10° C. over 20 min, and the reaction mixture was then boiled for 10 min, cooled, quenched with a mixture of ice and dilute hydrochloric acid and evaporated at reduced pressure. The residue was dissolved in dichloromethane, the solution washed with brine, dried with sodium sulphate and the solvent was evaporated under reduced pressure leaving a crystalline residue that was recrystallised from diethylether and petroleum ether. 1-(4-Benzyloxy-3-methoxyphenyl)-2-phenyl-1-ethanol was obtained as white crystals, m.p. 97 to 98° C.

Workup

  1. temperaturecooled
  2. customquenched with a mixture of ice and dilute hydrochloric acid
  3. customevaporated at reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washthe solution washed with brine
  6. dry with materialdried with sodium sulphate
  7. customthe solvent was evaporated under reduced pressure
  8. customleaving a crystalline residue that
  9. customwas recrystallised from diethylether and petroleum ether

Sources & evidence

ORD record
ord-42a9c01f1d6745ec82b8d496b2bc87a6
Source dataset
uspto-grants-2003_01
Patent number
US06512136B1

Reaction notes

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