3,5-Dimethoxyphenol → 1-(3-Chloropropoxy)-3,5-dimethoxybenzene

HRID 1193647Notes

Reaction equation

HRID 1193647 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl:12][CH:13](Br)[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:12][CH2:13][CH2:14][CH2:15][O:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 103833,5-DimethoxyphenolHCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-

Product 1

HCID 144071741-(3-Chloropropoxy)-3,5-dimethoxybenzeneYield 53.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,5-dimethoxyphenol, 100.0 g (0.6486 mole), chlorobromopropane, 148.0 g (0.96 mole) and potassium carbonate, 89.6 g (0.96 mole) was heated overnight at gentle reflux in 600 ml of acetone. The reaction mixture was cooled at room temperature, filtered, and stripped to dryness via a rotary evaporator. The resulting oil was dissolved in chloroform and the solution extracted with 5% aqueous sodium hydroxide; removal of chloroform gave a dark brown oil. A 5 g sample of the oil was pumped in vacuo overnight at 80° C. This produced 3.23 g (53.2% yield based on the aliquot taken) of dark brown oil.

Workup

  1. temperaturewas heated overnight
  2. filtrationfiltered
  3. customstripped to dryness via a rotary evaporator
  4. dissolutionThe resulting oil was dissolved in chloroform
  5. extractionthe solution extracted with 5% aqueous sodium hydroxide
  6. customremoval of chloroform
  7. customgave a dark brown oil
  8. customwas pumped in vacuo overnight at 80° C

Sources & evidence

ORD record
ord-4d609bf84bd64379bd1cbb2dcb27c8ca
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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