1-Bromo-3-chloropropane → HCID 56946192, compound

HRID 2042560Notes

Reaction equation

HRID 2042560 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][Cl:21]>CC(C)=O>[Cl:21][CH2:20][CH2:19][CH2:18][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 56946192HCID 56946192, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(4-hydroxyphenyl)ethanol (13.82 g, 100.0 mmol) and potassium carbonate (34.0 g, 250.0 mmol) in 125.0 mL of acetone was stirred as 1-bromo-3-chloropropane (24.0 g, 150.0 mmol) was added dropwise. The reaction was stirred at 60° C. overnight, and then filtered through celite, washed with acetone and concentrated. The residue was dissolved in EtOAc (250 mL) and washed with 2N Na2CO3, water, and saturated NaCl solution. After drying over Na2SO4 the solution was concentrated to give 21 g (98%): Mp 49-50° C.; MS m/z 197 (M−H).

Workup

  1. additionwas added dropwise
  2. filtrationfiltered through celite
  3. washwashed with acetone
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in EtOAc (250 mL)
  6. washwashed with 2N Na2CO3, water, and saturated NaCl solution
  7. dry with materialAfter drying over Na2SO4 the solution
  8. concentrationwas concentrated
  9. customto give 21 g (98%)

Sources & evidence

ORD record
ord-c6a5a9b4fb4a47d095434eabf5bfecd3
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

Loading…