Hydrochloric Acid → 2-[2-(Benzyloxy)ethyl]-6-methylbenzaldehyde

HRID 427519Notes

Reaction equation

HRID 427519 reaction equation
Br[C:2]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([Li])(C)(C)C.CN(C)[CH:26]=[O:27].Cl>O1CCCC1.C(OCC)C.O>[CH2:7]([O:6][CH2:5][CH2:4][C:3]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:2]=1[CH:26]=[O:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 18357451Benzyl 2-bromo-3-methylphenethyl etherHCID 178418306HCID 178418306, compound

Product 1

HCID 183574522-[2-(Benzyloxy)ethyl]-6-methylbenzaldehydeYield 38.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of benzyl 2-bromo-3-methylphenethyl ether (3.2 g, 0.0105 mol) in dry tetrahydrofuran in a nitrogen atmosphere at −65° C. was added tert-butyllithium (1.7 M in pentane)(10.5 ml, 0.018 mol) and the mixture was stirred at −20° C. for 30 min. Dimethylformamide (1.5 g, 0.021 mol) was added dropwise at −65° C. and the mixture was stirred at −20° C. for 30 min and at room temperature for 1 h. To the solution was water added carefully and 2M HCl to make it acidic and the mixture was stirred for 30 min. To the mixture was added diethyl ether (50 ml), the organic layer was separated, washed with saturated sodium carbonate and water. The organic layer was separated, dried and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using heptane:methylene chloride (2:8) as eluent gave 1.0 g (38.5%) of the title compound.

Workup

  1. stirringthe mixture was stirred at −20° C. for 30 min and at room temperature for 1 h
  2. additionadded carefully
  3. stirringthe mixture was stirred for 30 min
  4. customthe organic layer was separated
  5. washwashed with saturated sodium carbonate and water
  6. customThe organic layer was separated
  7. customdried
  8. customevaporated under reduced pressure
  9. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-048aff0038224998b57874ae1f72107f
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

Loading…