Catechol → 2-Ethyl-2-methyl-2H-1,3-benzodioxole

HRID 1033194Notes

Reaction equation

HRID 1033194 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][C:10](=O)[CH2:11][CH3:12].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)Cl>[CH2:10]([C:11]1([CH3:12])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1)[CH3:9]

Participants

5

Reactant 3

HCID 289CatecholHCID 6569Methyl Ethyl KetoneHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 126081602-Ethyl-2-methyl-2H-1,3-benzodioxoleYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 20.0 g (0.180 mole) of catechol and 0.8 g (0.40 mole) of 2-butanone in 200 ml of methylene chloride was added 128.0 g (0.902 mole) of phosphorus pentoxide. The reaction mixture was stirred at room temperature for two days. The stirring was stopped, and the reaction solids were allowed to settle. The reaction mixture was decanted into a separatory funnel. The solid material was washed with methylene chloride, and the wash was decanted into the above separatory funnel. The combined organic phase was washed with aqueous, saturated sodium bicarbonate solution. The washed organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure to yield 17.3 g of 2-ethyl-2-methyl-1,3-benzodioxole.

Workup

  1. customthe reaction solids
  2. customThe reaction mixture was decanted into a separatory funnel
  3. washThe solid material was washed with methylene chloride
  4. customthe wash was decanted into the above separatory funnel
  5. washThe combined organic phase was washed with aqueous, saturated sodium bicarbonate solution
  6. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  7. filtrationwas filtered
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-53234d56107a46d88ab508a0c58ab087
Source dataset
uspto-grants-1994_05
Patent number
US05310724

Reaction notes

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