3-Methoxybenzoic Acid → m-Anisoyl chloride

HRID 1389538Notes

Reaction equation

HRID 1389538 reaction equation
[C:1]([OH:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.S(Cl)([Cl:14])=O>CN(C)C=O>[C:1]([Cl:14])(=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 114613-Methoxybenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 74374m-Anisoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 100 g of m-anisic acid (0.658 mole), 250 g thionyl chloride (2.10 mole), and 5 ml dimethylformamide was heated under reflux in a round-bottom flask with desiccant in the top of the condenser for exclusion of atmospheric moisture. Excess thionyl chloride was distilled from the product using a rotary film-evaporator at about 200 torr (26.6 kPa). The m-anisoyl chloride was then isolated by fractional distillation through a 25 cm Vigreux column at 109° C./12 torr (1.6 kPa). Yield was 90 g (0.528 mole), i.e., about 80%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a round-bottom flask with desiccant in the top of the condenser for exclusion of atmospheric moisture
  3. distillationExcess thionyl chloride was distilled from the product
  4. customa rotary film-evaporator at about 200 torr (26.6 kPa)

Sources & evidence

ORD record
ord-94fea13e758f4846a3724a081ad15240
Source dataset
uspto-grants-1981_01
Patent number
US04245082

Reaction notes

Loading…