Hydrochloric Acid → 3-(4-Methoxyphenyl)-2-cyclohexen-1-one

HRID 2099938Notes

Reaction equation

HRID 2099938 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].C([O:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20](=O)[CH:19]=1)C.Cl>CCCCCC.C(OCC)C>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][C:11]([C:20]2[CH2:21][CH2:22][CH2:23][C:18](=[O:17])[CH:19]=2)=[CH:12][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 113582-BromoanisoleHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 178418339Butyllithium

Product 1

HCID 3679273-(4-Methoxyphenyl)-2-cyclohexen-1-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

100 ml of n-butyllithium 1.6M in hexane are added dropwise at 0° C. to a solution of 20 ml of bromoanisole in 600 ml of diethyl ether. After 2 hours, 20.2 ml of 3-ethoxy-2-cyclohexenone in 80 ml of diethyl ether are added dropwise. After 3 hours, 100 ml of 3N hydrochloric acid are added dropwise. The organic phase is separated off and concentrated, and the residue is purified over silica gel. 3-(4-Methoxyphenyl)-2-cyclohexen-1-one is obtained in the form of colourless crystals, m.p.: 83-85° C.

Workup

  1. waitAfter 3 hours
  2. customThe organic phase is separated off
  3. concentrationconcentrated
  4. customthe residue is purified over silica gel

Sources & evidence

ORD record
ord-e1accaeeaadf4d1481b658c26245c428
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

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