Methanol → 5-(Methoxycarbonyl)-2-methylbenzoic acid

HRID 2218936Notes

Reaction equation

HRID 2218936 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].S(Cl)(Cl)=O.N1C=CC=C[CH:19]=1.CO>CN(C=O)C.C(Cl)(Cl)(Cl)Cl>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]([OH:13])=[O:12])[CH:4]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 5957504-Methylbenzene-1,3-dicarboxylic acid

Product 1

HCID 229994865-(Methoxycarbonyl)-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of compound (2) (2.83 g, 15.71 mmol), thionyl chloride (50 ml) and DMF (3 drops) was heated at reflux for 2 hours. After cooling to room temperature, excess thionyl chloride was removed under reduced pressure (rotary evaporator). The dark oil which was obtained was dissolved in carbon tetrachloride (30 ml), treated with pyridine (1 ml, 12.43 mmol) and methanol (20 ml) and stirred at ambient temperature for 2 hours. The solvents were evaporated and the residue purified by flash chromatography: silica, hexane/EtOAc (9:1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customexcess thionyl chloride was removed under reduced pressure (rotary evaporator)
  4. customThe dark oil which was obtained
  5. customThe solvents were evaporated
  6. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-536b1eaad14c4f6e86df792ee6a87ba2
Source dataset
uspto-grants-2008_08
Patent number
US07413727B2

Reaction notes

Loading…