Trichloroacetic Acid → HCID 19102632, compound

HRID 1198387Notes

Reaction equation

HRID 1198387 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=2[O:2]1.[CH:11]([O:13][CH2:14][CH3:15])=[CH2:12].ClC(Cl)(Cl)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:11]([O:13][CH:14]([O:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[CH3:15])[CH3:12]

Participants

6

Reactant 4

HCID 6421Trichloroacetic AcidHCID 8023Ethyl vinyl etherHCID 14798Sodium HydroxideHCID 68289Sesamol

Product 1

HCID 19102632HCID 19102632, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 3,4-methylenedioxyphenol (6.0 g, 43.5 mmol), ethyl vinyl ether (3.75 g, 52.0 mmol) and a catalytic amount of trichloroacetic acid (50 mg, 0.3 mmol) in chloroform (50 ml) was stirred for two hours at room temperature. Aqueous NaOH (2N, 50 ml) was added and the resulting mixture was extracted with diethyl ether (3 times). The combined ether extracts were washed with aqueous NaOH (2N) and water, respectively, dried over Na2SO4, filtered and evaporated in vacuo to yield 5-(1-ethoxyethoxy)-1,3-benzodioxole (8.96 g, 98% yield; compound No. 1) as an oil.

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether (3 times)
  2. washThe combined ether extracts were washed with aqueous NaOH (2N) and water
  3. dry with materialrespectively, dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a9e91d41ef9e4451a01bab9c65f2f847
Source dataset
uspto-grants-1994_01
Patent number
US05281595

Reaction notes

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