Hydrochloric Acid → 2,3,4,5-Tetramethoxy-6-methylphenylmethanol

HRID 2268490Notes

Reaction equation

HRID 2268490 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[C:14]([O:21][CH3:22])=[C:13]([CH3:23])[C:10]=1[CH:11]=[O:12].Cl>C(OCC)C.O>[CH3:7][O:8][C:9]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[C:14]([O:21][CH3:22])=[C:13]([CH3:23])[C:10]=1[CH2:11][OH:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 183485582,3,4,5-Tetramethoxy-6-methylphenylmethanolYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (2.37 g) in diethyl ether (150 ml) was dropwise added a solution of 2,3,4,5-tetramethoxy-6-methylbenzaldehyde (15.0 g) in diethyl ether (30 ml) with cooling with ice. After the reaction mixture was stirred for 30 min, 10% hydrochloric acid was added to the reaction mixture, which was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=2:1) to yield the entitled compound (14.2 g) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-aaf9a45f311b4f919725c32da4e7aed4
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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