Water → 2-[(2-Bromophenyl)methyl]-6-[(phenylmethoxy)methyl]-cyclohexanone

HRID 1460606Notes

Reaction equation

HRID 1460606 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1CCCC1.[Br:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br.O>C1C=CC=CC=1>[Br:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][CH:12]1[CH2:13][CH2:14][CH2:15][CH:10]([CH2:9][O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]1=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 769652-Bromobenzyl bromideHCID 10489011Cyclohexanone, 2-[(phenylmethoxy)methyl]-

Product 1

HCID 198011362-[(2-Bromophenyl)methyl]-6-[(phenylmethoxy)methyl]-cyclohexanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the ketone of Example 113 in benzene is added pyrrolidine (4 equivalents). The mixture is heated to reflux for 24 hours removing the water formed by use of a Dean-Stark type apparatus. The reaction mixture is concentrated in vacuo. The organics are dissolved in dioxane followed by addition of 2-bromobenzyl bromide (1.5 equivalents). The mixture is heated to reflux for 6 hours. Water is added and the refluxing continued for 3 hours. The solution is concentrated in vacuo to dryness. The remaining organics are partitioned between ether and water. The ether layer is dried (MgSO4), concentrated in vacuo, then chromatographed to give the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 hours
  3. customremoving the water
  4. customformed by use of a Dean-Stark type apparatus
  5. concentrationThe reaction mixture is concentrated in vacuo
  6. dissolutionThe organics are dissolved in dioxane
  7. temperatureThe mixture is heated
  8. temperatureto reflux for 6 hours
  9. concentrationThe solution is concentrated in vacuo to dryness
  10. customThe remaining organics are partitioned between ether and water
  11. dry with materialThe ether layer is dried (MgSO4)
  12. concentrationconcentrated in vacuo
  13. customchromatographed

Sources & evidence

ORD record
ord-eb81b68a4b3247419ef4cd02f179247a
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

Loading…