Catechol → HCID 19363527, compound

HRID 2398309Notes

Reaction equation

HRID 2398309 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[Na].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].O>C(O)C>[CH2:11]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 289CatecholHCID 962WaterHCID 80571-BromopentaneHCID 5360545Sodium

Product 1

HCID 19363527HCID 19363527, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

110 g (1 mole) of catechol was added to a solution of 23 g (1 mole) of metallic sodium in 1 liter of absolute ethanol and the mixture was stirred under nitrogen for one hour. Then, 166 g (1.1 mole) of 1-bromopentane were added dropwise to the mixture over 15 minutes and the mixture was refluxed with stirring for 3 hours, was cooled and poured into 3 liters of water. The mixture was extracted with 1000 ml of ether and the ether extracts were washed with 20% sodium carbonate solution and then water, dried over magnesium sulfate and evaporated to dryness under reduced pressure to obtain 157 g of 2-(n-pentyloxy)-phenol as a yellow oil. IR spectrum showed OH at 3540 cm - 1.

Workup

  1. temperaturethe mixture was refluxed
  2. stirringwith stirring for 3 hours
  3. temperaturewas cooled
  4. extractionThe mixture was extracted with 1000 ml of ether
  5. washthe ether extracts were washed with 20% sodium carbonate solution
  6. dry with materialwater, dried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ff6cbea3a4c74d858ce723deaac8f00c
Source dataset
uspto-grants-1977_05
Patent number
US04024276

Reaction notes

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