Catechol → o-(1-Methoxyethoxy)-phenol

HRID 1390872Notes

Reaction equation

HRID 1390872 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][O:10][CH:11]=[CH2:12].[OH-].[Na+]>Cl.C1(C)C=CC=CC=1>[CH3:9][O:10][CH:11]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])[CH3:12]

Participants

6

Reactant 3

HCID 289CatecholHCID 7861Methyl vinyl etherHCID 14798Sodium Hydroxide

Product 1

HCID 20431181o-(1-Methoxyethoxy)-phenol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 1140TolueneSolvent

Procedure

110 parts by weight of pyrocatechol is suspended in 100 parts by weight of toluene. At +5° C. 64 parts by weight of vinyl methyl ether which has a temperature of -40° C. is poured in all at once and then 1 drop of concentrated hydrochloric acid is added. The whole is heated to about +20° C. while stirring, whereupon the reaction commences and the temperature of the contents of the flask rises to about 65° C. External cooling with ice-water may be applied if necessary. The whole is kept for half an hour at 65° C. and then 5 parts by weight of 2-normal caustic soda solution is added. The whole is cooled, and dried by means of sodium sulfate, and the solvent is evaporated in a rotary evaporator. The product is distilled in vacuo. The yield is 155 parts by weight. The boiling point is 85° to 90° C. at 0.5 mm.

Workup

  1. customAt +5° C
  2. customa temperature of -40° C.
  3. additionis added
  4. temperatureThe whole is heated to about +20° C.
  5. customrises to about 65° C
  6. waitThe whole is kept for half an hour at 65° C.
  7. temperatureThe whole is cooled
  8. dry with materialdried by means of sodium sulfate
  9. customthe solvent is evaporated in a rotary evaporator
  10. distillationThe product is distilled in vacuo

Sources & evidence

ORD record
ord-a74cef212e5849bc8d0971a55cfd35c1
Source dataset
uspto-grants-1979_02
Patent number
US04140725

Reaction notes

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