Methanol → Benzoic acid, 2-hydroxy-5-iodo-3-methyl-, methyl ester

HRID 1916565

Reaction equation

HRID 1916565 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:17]O>>[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 159086852-Hydroxy-5-iodo-3-methylbenzoic acid

Product 1

HCID 14172484Benzoic acid, 2-hydroxy-5-iodo-3-methyl-, methyl ester

Procedure

A solution of 2.0 g (7.19 mmol) 2-hydroxy-5-iodo-3-methyl-benzoic acid in 5.0 mL thionyl chloride (69.0 mmol) is stirred for 20 min at 80° C. Thionyl chloride is eliminated i.vac. and the residue is combined with 20 mL MeOH and stirred for 20 min at RT. The product is precipitated out of the reaction. MeOH is eliminated i.vac. down to 5 mL and the residue is suction filtered. The product is further reacted without any more purification.

Workup

  1. customThe product is precipitated out of the reaction
  2. filtrationfiltered
  3. customThe product is further reacted without any more purification

Sources & evidence

ORD record
ord-14bc186e27e24c299a0c3914c5a30543
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Linked notes

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