Thionyl Chloride → HCID 10035354, compound

HRID 1534419Notes

Reaction equation

HRID 1534419 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-56d2b0da3af145f2a526f46e6ee93563
Source dataset
uspto-grants-1992_02
Patent number
US05089505

Reaction notes

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