Homovanillyl alcohol → 4-Hydroxy-3-methoxyphenethyl chloride

HRID 21406

Reaction equation

HRID 21406 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11]O)=[CH:8][C:7]=1[O:15][CH3:16]>ClCCl>[OH:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][CH2:11][Cl:3])=[CH:8][C:7]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 16928Homovanillyl alcoholHCID 24386Thionyl Chloride

Product 1

HCID 212240924-Hydroxy-3-methoxyphenethyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.5 ml) was added, dropwise, to a! stirred solution of 4-hydroxy-3-methoxyphenethyl alcohol (0.83 g--commercially available) in dichloromethane (50 ml). When the addition was complete, the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 2%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 0.36 g.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. concentrationthe mixture was concentrated in vacuo
  5. customto give a gum which
  6. customwas purified by column chromatography on silica eluting with dichloromethane
  7. additioncontaining methanol (0% up to 2%)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-124c450056884168846253c87de29ffb
Source dataset
uspto-grants-1995_06
Patent number
US05422358

Linked notes

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