Hexane → 5-(Benzyloxy)-4-methoxy-2-methylbenzaldehyde

HRID 1835409Notes

Reaction equation

HRID 1835409 reaction equation
CCCCCC.C([Li])CCC.[CH2:12]([O:19][C:20]1[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22](Br)[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+].[C:32](OCC)(=[O:34])C>CN(C)C=O.O1CCCC1>[CH2:12]([O:19][C:20]1[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]([CH:21]=1)[CH:32]=[O:34])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 121515384-Benzyloxy-2-bromo-5-methoxytolueneHCID 178418339Butyllithium

Product 1

HCID 121515395-(Benzyloxy)-4-methoxy-2-methylbenzaldehydeYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A hexane solution (17 ml) of n-butyllithium was dropwise added to a tetrahydrofuran (190 ml) solution of 4-benzyloxy-2-bromo-5-methoxytoluene (7.83 g) at −78° C. over a period of 20 minutes, followed by stirring at the same temperature for 1 hour. A tetrahydrofuran (10 ml) solution of dimethylformamide (3.73 g) was dropwise added thereto at −78° C., followed by stirring at the same temperature for 1 hour. The temperature was gradually raised to room temperature, and stirring was further carried out for one night. The reaction solution was poured into an aqueous ammonium chloride solution (200 ml), and extraction with ethyl acetate (150 ml) was carried out twice. The ethyl acetate phase was washed with an aqueous sodium chloride solution (100 ml) twice and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 3.14 g (yield 48%) of 5-benzyloxy-4-methoxy-2-methylbenzaldehyde (m.p. 107-109° C.), and its structure was confirmed by nuclear magnetic resonance spectrum.

Workup

  1. customat −78° C.
  2. stirringby stirring at the same temperature for 1 hour
  3. stirringstirring
  4. waitwas further carried out for one night
  5. washThe ethyl acetate phase was washed with an aqueous sodium chloride solution (100 ml) twice
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0a074ff3fef34f8dbf03272e1e57eef3
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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