Sodium Hydroxide → HCID 17964265, compound

HRID 1374971Notes

Reaction equation

HRID 1374971 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][CH2:10][O:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:17](OCOCCOC)=[O:18].[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][CH2:9][CH2:10][O:11][CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[CH3:29])[CH:17]=[O:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 17964134HCID 17964134, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 17964265HCID 17964265, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.35 g) was added by small portions over 12 minutes to an ice-cooled solution of (2-methoxyethoxy)methyl 3-[(2-methoxyethoxy)methoxy]-4-methylbenzoate (3.5 g) in tetrahydrofuran (20 ml) below 5° C. under nitrogen atmosphere. After the mixture was stirred at the same temperature for 30 minutes, 2N sodium hydroxide (0.5 ml) was added to the mixture. After the mixture was stirred for 30 minutes, the insoluble materials were removed by filtration and washed with tetrahydrofuran. The filtrate and the washing were combined, and evaporated under reduced pressure. The residue was dissolved into ethyl acetate, and manganese (IV) oxide (3.5 g) was added to the solution. After being stirred under reflux for 2 hours, the reaction mixture was filtered through Celite® and the insoluble mass was washed with ethyl acetate. The filtrate and the washing were combined and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using mixed solvents of hexane and ethyl acetate (10:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give 3-[(2-methoxyethoxy)methoxy]-4-methylbenzaldehyde (1.7 g) as an oil.

Workup

  1. stirringAfter the mixture was stirred for 30 minutes
  2. customthe insoluble materials were removed by filtration
  3. washwashed with tetrahydrofuran
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved into ethyl acetate, and manganese (IV) oxide (3.5 g)
  6. additionwas added to the solution
  7. stirringAfter being stirred
  8. temperatureunder reflux for 2 hours
  9. filtrationthe reaction mixture was filtered through Celite®
  10. washthe insoluble mass was washed with ethyl acetate
  11. customevaporated under reduced pressure
  12. customThe resulting residue was purified by column chromatography on silica gel using
  13. additionmixed solvents of hexane and ethyl acetate (10:1)
  14. additionThe fractions containing the objective compound
  15. customwere collected
  16. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c29914a0c772441b9a936215f05abedc
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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