Catechol → Phenol, 2-(methoxymethoxy)-

HRID 65900Notes

Reaction equation

HRID 65900 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(N(CC)CC)C.[CH3:16][O:17][CH2:18]Cl>C1C=CC=CC=1>[CH3:16][O:17][CH2:18][O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 289CatecholHCID 7864Chloromethyl Methyl EtherHCID 8471Triethylamine

Product 1

HCID 10374647Phenol, 2-(methoxymethoxy)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

110 parts by weight of pyrocatechol is dissolved in 400 parts by weight of benzene. At room temperature there are simultaneously dripped into this solution 101 parts by weight of triethylamine and 81 parts by weight of chloromethyl methyl ether in such a manner that the reaction medium has a weakly alkaline reaction. Subsequently the mixture is heated for an hour under reflux and then allowed to cool. The hydrochloride is removed by suction filtration and the product is washed, dried over Na2SO4, concentrated and distilled in vacuo.

Workup

  1. customAt room temperature
  2. customa weakly alkaline reaction
  3. temperatureSubsequently the mixture is heated for an hour
  4. temperatureunder reflux
  5. temperatureto cool
  6. customThe hydrochloride is removed by suction filtration
  7. washthe product is washed
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-63993e59c0d544509b6dba3eb3acab31
Source dataset
uspto-grants-1978_12
Patent number
US04129601

Reaction notes

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