2,5-Dimethoxy-3,4,6-trimethylbenzaldehyde → (2,5-Dimethoxy-3,4,6-trimethylphenyl)methanol

HRID 232072Notes

Reaction equation

HRID 232072 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][CH3:14])=[C:7]([CH3:15])[C:4]=1[CH:5]=[O:6].[Na]>C(O)C>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][CH3:14])=[C:7]([CH3:15])[C:4]=1[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 27526052,5-Dimethoxy-3,4,6-trimethylbenzaldehydeHCID 5360545Sodium

Product 1

HCID 13389492(2,5-Dimethoxy-3,4,6-trimethylphenyl)methanolYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 20 g (96 mmol) of 2,5-dimethoxy-3,4,6-trimethylbenzaldehyde in 200 ml of ethanol, 1.8 g (47.6 mmol) of sodium boronhydride was added and stirred for 30 minutes. To the reaction mixture saline was added, and the product was extracted with ethyl acetate. The extract was washed with water and dried, from which the solvent was evaporated off under reduced pressure. The residue was crystallized from isopropyl ether, to give 18.6 g (92.1%) of 2,5-dimethoxy-3,4,6-trimethylbenzylalcohol. m.p. 121°-122° C.

Workup

  1. additionTo the reaction mixture saline was added
  2. extractionthe product was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried, from which the solvent
  5. customwas evaporated off under reduced pressure
  6. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-82fe5d226e1d45d0bdf5617410687f23
Source dataset
uspto-grants-1989_07
Patent number
US04851413

Reaction notes

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