Catechol → 1,4-Benzodioxane-2-methanol

HRID 2417796Notes

Reaction equation

HRID 2417796 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH2:9]([CH:11]1[O:13][CH2:12]1)Cl.[OH-].[K+]>>[OH:13][CH2:12][CH:11]1[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2][CH2:9]1

Participants

4

Reactant 3

HCID 289CatecholHCID 7835EpichlorohydrinHCID 14797Potassium Hydroxide

Product 1

HCID 193141,4-Benzodioxane-2-methanol

Procedure

0.5 mole of pyrocatechol were stirred vigorously with 1.5 moles of epichlorohydrin and 1 mole of 10% strength aqueous potassium hydroxide solution at 100° C. After the mixture had been cooled, it was extracted with ether, the ether extract was washed with dilute potassium hydroxide solution and water, dried and evaporated and the product was recrystallized from ethanol. Melting point: 87°-90° C.

Workup

  1. temperatureAfter the mixture had been cooled
  2. extractionit was extracted with ether
  3. extractionthe ether extract
  4. washwas washed with dilute potassium hydroxide solution and water
  5. customdried
  6. customevaporated
  7. customthe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-56e20d4698e74f0c8529137a23e2a84b
Source dataset
uspto-grants-1984_09
Patent number
US04470989

Reaction notes

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