Catechol → HCID 10955985, compound

HRID 388187Notes

Reaction equation

HRID 388187 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[OH-].[K+].[CH3:11][CH:12]([CH3:16])[CH2:13][CH2:14]Br>C(O)C>[CH3:11][CH:12]([CH3:16])[CH2:13][CH2:14][O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH2:14][CH2:13][CH:12]([CH3:16])[CH3:11]

Participants

5

Reactant 3

HCID 289CatecholHCID 78911-Bromo-3-methylbutaneHCID 14797Potassium Hydroxide

Product 1

HCID 10955985HCID 10955985, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of catechol (27.53 g, 0.25 mol) in 100 ml of ethanol was slowly added to a stirred solution of KOH (35.07 g, 0.63 mol) in 350 ml of ethanol at room temperature. The reaction mixture was stirred for 1 h. A solution of 3-methylbutyl bromide (113.25 g, 0.75 mol) in 50 ml of ethanol was added dropwise. The reaction mixture was refluxed overnight. Ethanol was removed by rotary evaporation and the reaction mixture was partitioned between ethyl acetate and sodium carbonate solution. After drying over sodium sulfate, the product was obtained by reduced pressure distillation to get 38.2 g 1,2-bis(3′-methylbutoxy)benzene (61%). NMR (ppm) (400 MHz, CDCl3): δ 6.914 (s, 4H), 4.059-4.025 (t, 4H), 1.895-1.861 (m, 2H), 1.757-1.707 (m, 4H), 0.993-0.976 (m, 12H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customEthanol was removed by rotary evaporation
  3. customthe reaction mixture was partitioned between ethyl acetate and sodium carbonate solution
  4. dry with materialAfter drying over sodium sulfate
  5. customthe product was obtained by reduced pressure distillation

Sources & evidence

ORD record
ord-ae4b829309cd4f61b4b03c29e98e460b
Source dataset
uspto-grants-2013_02
Patent number
US08377570B2

Reaction notes

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