Catechol → Butyl ether

HRID 2291143Notes

Reaction equation

HRID 2291143 reaction equation
C1([C:3](=[CH:5][CH:6]=[CH:7]C=1)[OH:4])O.[C:9](Cl)(=O)[C:10](Cl)=O.[CH2:15](OCC)[CH3:16]>C1(C)C=CC=CC=1.O1CCOCC1>[CH2:15]([O:4][CH2:3][CH2:5][CH2:6][CH3:7])[CH2:16][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 289Catechol2×HCID 3283Diethyl EtherHCID 65578Oxalyl chloride

Product 1

HCID 8909Butyl ether

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

1 mole of pyrocatechol or pyrocatechol derivatives (see Table 1) in a mixture of 500 ml of toluene and 50 ml of dioxane was taken and 1.05 mole of oxalyl chloride were added dropwise at 70° C. Thereafter, the mixture was subsequently stirred until the evolution of gas had ended. After the reaction mixture had cooled to room temperature, it was filtered and the solid product was dried in vacuo. The same results were obtained when diethyl ether or dibutyl ether was used instead of the toluene/dioxane mixture. The starting materials and the results are summarized in Table 1.

Workup

  1. filtrationit was filtered
  2. customthe solid product was dried in vacuo
  3. customThe same results

Sources & evidence

ORD record
ord-ee0eb1786fff45d0bb79baffb2517a5a
Source dataset
uspto-grants-1986_10
Patent number
US04620018

Reaction notes

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