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

HRID 875413

반응식

HRID 875413 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d82c72fb81b846f0b43003ab6ef27537
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980911B2

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