Catechol → HCID 19363527, compound

HRID 1597716Notes

Reaction equation

HRID 1597716 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10])[OH:8].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(C(C)=O)C(C)C>[OH:8][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[O:10][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 289CatecholHCID 80571-BromopentaneHCID 11430Potassium Carbonate

Product 1

HCID 19363527HCID 19363527, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

95.1 g (0.69 mol) of potassium carbonate and 321.2 g of methyl isobutyl ketone were added to 137.64 g (1.25 mol) of pyrocatechol and 188.63 g (1.25 mol) of 1-bromopentane, and the mixture was then refluxed for 23 hours. The mixture was cooled, after which the potassium carbonate was filtered off and the methyl isobutyl ketone was distilled off under reduced pressure. The oily residue was then subjected to fractional distillation over a short column under reduced pressure from an oil pump. 127.3 g of 1-hydroxy-2-pentoxybenzene were obtained at 5 bar and a boiling point of 88°-92° C.

Workup

  1. temperaturethe mixture was then refluxed for 23 hours
  2. temperatureThe mixture was cooled
  3. filtrationafter which the potassium carbonate was filtered off
  4. distillationthe methyl isobutyl ketone was distilled off under reduced pressure
  5. distillationThe oily residue was then subjected to fractional distillation over a short column under reduced pressure from an oil pump

Sources & evidence

ORD record
ord-5cdecbda9ae347eba03abeb62e36cf0e
Source dataset
uspto-grants-1998_04
Patent number
US05736068

Reaction notes

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