3-Methoxybenzoic Acid → m-Anisoyl chloride

HRID 2287219Notes

Reaction equation

HRID 2287219 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

This intermediate was prepared by either of two methods. In the first, a mixture of 100 g of m-anisic acid (0.658 mole), 250 g thionyl chloride (2.10 mole), and 5 mL of 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 26.6 kPa pressure. The m-anisoyl chloride was then isolated by fractional distillation through a 25 cm Vigreux column at 109° C. and 1.6 kPa pressure.

Workup

  1. customThis intermediate was prepared by either of two methods
  2. temperaturewas heated
  3. temperatureunder reflux in a round-bottom flask with desiccant in the top of the condenser for exclusion of atmospheric moisture
  4. distillationExcess thionyl chloride was distilled from the product
  5. customa rotary film-evaporator at about 26.6 kPa pressure

Sources & evidence

ORD record
ord-786a95810aa040148fe8176feeef810b
Source dataset
uspto-grants-1981_05
Patent number
US04269965

Reaction notes

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