Resorcinol → HCID 15125718, compound

HRID 30954Notes

Reaction equation

HRID 30954 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:9][O-].[Na+].Br[C:13]1[CH:14]=[C:15]([O:19]C)[CH:16]=[CH:17][CH:18]=1>N1C=CC=CC=1.CO.Cl[Cu]>[CH3:9][O:2][C:1]1[CH:3]=[C:4]([O:5][C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 5054ResorcinolHCID 169713-BromoanisoleHCID 10942334Sodium Methoxide

Product 1

HCID 15125718HCID 15125718, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

In a round-bottomed flask fitted with a Vigreux column, a reflux divider and a condenser, 77.08 g (0.70 mol.) of resorcinol are dissolved, under argon, in 250 ml of dry pyridine. 84.3 g of sodium methoxide solution in methanol (30% solution) are added dropwise to the reaction mixture, with stirring. Methanol is then removed from the reaction mixture by distillation. The reflux divider is then closed and 261.9 g (1.40 mol.) of 3-bromoanisole are added dropwise. 3.5 g (0.04 mol.) of CuCl are also added. The mixture is allowed to boil under reflux for 6 hours. Pyridine is then distilled off via the opened reflux divider, during which the sump temperature rises to 150° C. The mixture is then allowed to cool and the residue is stirred into 250 ml of semi-concentrated hydrochloric acid. The mixture is extracted with 300 ml of toluene. The organic phase is washed first with semi-concentrated hydrochloric acid and then a further two times with NaOH solution (10%). The combined alkaline phases are acidified with dilute HCl and extracted with a diethyl ether/toluene mixture (1:1). After removal of the solvent, 65.5 g of a brown oil are obtained.

Workup

  1. customIn a round-bottomed flask fitted with a Vigreux column
  2. customMethanol is then removed from the reaction mixture by distillation
  3. customThe reflux divider is then closed
  4. temperatureunder reflux for 6 hours
  5. distillationPyridine is then distilled off via the
  6. temperatureopened reflux divider
  7. customrises to 150° C
  8. temperatureto cool
  9. stirringthe residue is stirred into 250 ml of semi-concentrated hydrochloric acid
  10. extractionThe mixture is extracted with 300 ml of toluene
  11. washThe organic phase is washed first with semi-concentrated hydrochloric acid
  12. extractionextracted with a diethyl ether/toluene mixture (1:1)
  13. customAfter removal of the solvent, 65.5 g of a brown oil
  14. customare obtained

Sources & evidence

ORD record
ord-18cd8352ede64afc959c89f942d78e33
Source dataset
uspto-grants-2008_09
Patent number
US07425358B2

Reaction notes

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