Thionyl Chloride → Methyl 3-tert-butyl-5-(chlorocarbonyl)benzoate

HRID 2360023Notes

Reaction equation

HRID 2360023 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:13]=1)[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:20])=O>CN(C=O)C.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:13]=[C:12]([CH:11]=[C:7]([C:8]([Cl:20])=[O:9])[CH:6]=1)[C:14]([O:16][CH3:17])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 121446585-tert-Butyl-isophthalic acid monomethyl ester

Product 1

HCID 86652123Methyl 3-tert-butyl-5-(chlorocarbonyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-tert-butyl-5-(methoxycarbonyl)benzoic acid (9.18 g, 38.9 mmol, prepared by the method of Carter et. al., WO2005021500A1), thionyl chloride (75 mL) and 1 drop of DMF in toluene (200 mL) was heated at reflux for 2 h, cooled and concentrated. The residue was azeotroped with toluene (3×50 mL) and dried under high vacuum to give the title compound as an off-white waxy solid (9.9 g, quantitative yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue was azeotroped with toluene (3×50 mL)
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-6aa3a2a688f1444ca4191ffa3bbadd05
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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