Guaiacol → HCID 54555031, compound

HRID 1613435Notes

Reaction equation

HRID 1613435 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][OH:9].C1(OC)C(=CC=CC=1)O.BrCCCO.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.[S:41](Cl)(=[O:44])(=[O:43])[NH2:42]>CC(C)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][O:9][S:41](=[O:44])(=[O:43])[NH2:42]

Participants

9

Reactant 6

HCID 460GuaiacolHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 24499Chlorosulfamic acidHCID 13629100HCID 13629100, compound

Product 1

HCID 54555031HCID 54555031, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 13.0 g (0.071 mole) of 3-(2-methoxyphenoxy)-1-propanol (prepared in 68% yield from guaiacol (43.2 g, 0.35 mole), 3-bromo-1-propanol (89.3 g, 0.61 mole) and potassium carbonate (112.0 g, 0.81 mole) in 1 l of acetone and 9.0 g (0.089 mole) of triethylamine in 50 ml of methylene chloride was added dropwise (20 min.) to a stirred, cooled (ice-acetone bath) solution of 22 ml (0.0786 mole) of sulfamoyl chloride (3.57M solution in acetonitrile, Preparation 19) in 30 ml methylene chloride at such a rate the temperature was maintained at ≤12° C. The reaction mixture was stirred at ambient temperature for 3 hr. The solvents were evaporated under reduced pressure and the viscous residue was triturated with 300 ml of ethyl acetate and the solids removed by filtration. The filtrate was washed with three 300 ml portions of water, dried (magnesium sulfate) and the solvent evaporated under reduced pressure to yield 11.7 g (63%) of a colorless, viscous oil that solidified upon standing. The solid was recrystallized from methylene chloride-petroleum ether (30°-60° C.) to give 6.9 g (37%) of the title compound as a white solid, mp 80°-83° C.

Workup

  1. additionwas added dropwise (20 min.) to a stirred
  2. temperaturewas maintained at ≤12° C
  3. customThe solvents were evaporated under reduced pressure
  4. customthe viscous residue was triturated with 300 ml of ethyl acetate
  5. customthe solids removed by filtration
  6. washThe filtrate was washed with three 300 ml portions of water
  7. dry with materialdried (magnesium sulfate)
  8. customthe solvent evaporated under reduced pressure
  9. customto yield 11.7 g (63%) of a colorless, viscous oil that
  10. customThe solid was recrystallized from methylene chloride-petroleum ether (30°-60° C.)

Sources & evidence

ORD record
ord-9f85cc33f0f14f65a7652d4ab03279f4
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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