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

HRID 875413ノート

反応式

HRID 875413 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d82c72fb81b846f0b43003ab6ef27537
出典データセット
uspto-grants-2015_03
特許番号
US08980911B2

反応ノート

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