Thionyl Chloride → HCID 10035354, compound

HRID 484327Notes

Reaction equation

HRID 484327 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:5][CH2:6]O.S(Cl)([Cl:15])=O>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:5][CH2:6][Cl:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 100349913-hydroxy-4-methoxybenzeneethanol

Product 1

HCID 10035354HCID 10035354, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-hydroxy-4-methoxyphenethyl alcohol (2.25 g) and thionyl chloride (5 ml) in methylene chloride (120 ml) was heated under reflux for 16 hours and evaporated. The residue was azeotroped twice with hexane and purified by chromatography on silica (30 g) using methylene chloride plus 0-6% methanol as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless solid (0.82 g, 33%), m.p. 53°-54°, which was characterised by its 1H-n.m.r. spectrum.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customevaporated
  4. customThe residue was azeotroped twice with hexane
  5. custompurified by chromatography on silica (30 g)
  6. customevaporated

Sources & evidence

ORD record
ord-988a9adff7e94116a94625c36d377fc4
Source dataset
uspto-grants-1993_07
Patent number
US05231104

Reaction notes

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