Guaiacol → 1-(2-Chloroethoxy)-2-methoxybenzene

HRID 617107Notes

Reaction equation

HRID 617107 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].O1CCCC1.C[O-].[Na+].[Cl:18][CH2:19][CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:20][CH2:19][Cl:18]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 8028Tetrahydrofuran3×HCID 10942334Sodium Methoxide

Product 1

HCID 41438391-(2-Chloroethoxy)-2-methoxybenzeneYield 67.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

24.83 g (0.2 mole) of o-methoxyphenol and 100 ml of tetrahydrofuran were placed in a 500 ml-flask equipped with a stirring device and a cooling pipe. A solution in which sodium methoxide (0.2 mole) was dissolved in methanol was added to the flask while stirring the contents. Then tetrahydrofuran and methanol were eliminated at reduced pressure. 300 ml of tetrahydrofuran was added to the flask and then 46.94 g (0.2 mole) of 2-chloroethyl-p-toluene sulfonate was added thereto. The mixture was then stirred under heating reflux for 20 hours to promote reaction. After reaction, insoluble matters were eliminated by filtration, and the product was condensed at reduced pressure. The reaction mixture was then refined by column chromatography using silica gel, and 25.1 g of 2-(o-methoxyphenoxy)ethyl chloride was produced.

Workup

  1. customequipped with a stirring device
  2. additionwas added to the flask
  3. stirringThe mixture was then stirred
  4. temperatureunder heating
  5. temperaturereflux for 20 hours
  6. customreaction
  7. customAfter reaction, insoluble matters
  8. filtrationwere eliminated by filtration
  9. customcondensed at reduced pressure

Sources & evidence

ORD record
ord-496dea0132c24241ab647e5868946a12
Source dataset
uspto-grants-1999_09
Patent number
US05948590

Reaction notes

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