Sodium Acetate → (2,5-Dimethoxy-3,4-dimethylphenyl)methyl acetate

HRID 1252983Notes

Reaction equation

HRID 1252983 reaction equation
Cl[CH2:2][C:3]1[C:4]([O:13][CH3:14])=[C:5]([CH3:12])[C:6]([CH3:11])=[C:7]([O:9][CH3:10])[CH:8]=1.[C:15]([O-:18])(=[O:17])[CH3:16].[Na+]>C(O)(=O)C.O>[C:15]([O:18][CH2:2][C:3]1[C:4]([O:13][CH3:14])=[C:5]([CH3:12])[C:6]([CH3:11])=[C:7]([O:9][CH3:10])[CH:8]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 13296937HCID 13296937, compound

Product 1

HCID 148394(2,5-Dimethoxy-3,4-dimethylphenyl)methyl acetateYield 93.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of intermediate C (5 g, 0.023 mole) and anhydrous sodium acetate (7.1 g, 0.086 mole) in glacial acetic acid (35 ml) was refluxed for 20 hours. The reaction mixture was cooled to room temperature, diluted with 50 ml of water and extracted with dichloromethane. The organic extracts were washed with saturated sodium bicarbonate solution, dried, and concentrated to yield a dark syrup, which eventually crystallized to give 5.1 g of crude 5-acetoxymethyl-1,4-dimethoxy-2,3-dimethylbenzene (intermediate D).

Workup

  1. temperaturewas refluxed for 20 hours
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with saturated sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated
  6. customto yield a dark syrup, which
  7. customeventually crystallized

Sources & evidence

ORD record
ord-1669fdd8bbfc4a3fbf43b3e9b76b3a08
Source dataset
uspto-grants-1988_05
Patent number
US04746607

Reaction notes

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