Lithium iodide → 2,6-Dichloro-4-(hydroxymethyl)benzoic acid

HRID 2201806Notes

Reaction equation

HRID 2201806 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[C:8]([Cl:14])[C:3]=1[C:4]([O:6]C)=[O:5].[I-].[Li+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[C:8]([Cl:14])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 66712920Methyl 2,6-dichloro-4-(hydroxymethyl)benzoate

Product 1

HCID 667205832,6-Dichloro-4-(hydroxymethyl)benzoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of methyl 2,6-dichloro-4-(hydroxymethyl)benzoate (5.3 g, 22 mmol) in pyridine (20 mL) was treated with anhydrous lithium iodide (9 g, 67 mmol). The resulting reaction mixture was heated to reflux for 5 hours, cooled to room temperature and concentrated under vacuum. The residue was diluted with water and acidified with dilute hydrochloric acid (pH 2-3) and partitioned with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, concentrated and the residue obtained upon triturating with diethyl ether afforded 2,6-dichloro-4-(hydroxymethyl)benzoic acid as a pale yellow solid (3.5 g, 70%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 5 hours
  4. concentrationconcentrated under vacuum
  5. additionThe residue was diluted with water
  6. custompartitioned with ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customthe residue obtained
  11. customupon triturating with diethyl ether

Sources & evidence

ORD record
ord-4f0aa3b127d040988b31bce8d5e8d53f
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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