Acetic Acid → 3-(propan-2-yloxy)phenol

HRID 427387Notes

Reaction equation

HRID 427387 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH2:9]1[CH2:19]CN2C(=NCCC2)C[CH2:10]1.C(Br)(C)C.C(O)(=O)C>C1COCC1>[CH:9]([O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1)([CH3:19])[CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5054ResorcinolHCID 63582-BromopropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 2353733-(propan-2-yloxy)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of THF, 1.5 g of resorcinol was dissolved and 2.24 ml of DBU was added under ice cooling. The resultant mixture was stirred for 10 min at room temperture. To the mixture, 1.92 ml of isopropyl bromide was added and refluxed for 2 hr. The reaction mixture was neutralized with acetic acid and evaporated under reduced pressure. The evaporated residue was redissolved in ethyl acetate and washed with 5% aqueous citric acid solution and saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure and the residue was subjected to a silica gel column chromatography (chloroform:methanol=40:1) to give 466 mg of the title compound.

Workup

  1. temperaturerefluxed for 2 hr
  2. customevaporated under reduced pressure
  3. dissolutionThe evaporated residue was redissolved in ethyl acetate
  4. washwashed with 5% aqueous citric acid solution and saturated aqueous sodium chloride solution
  5. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  6. customThe dried solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-22209b4ada514a8caf4738689a9f9d51
Source dataset
uspto-grants-2001_11
Patent number
US06313094B1

Reaction notes

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