Methanol → Methyl 2,6-dichloro-4-(hydroxymethyl)benzoate

HRID 2201805

반응식

HRID 2201805 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14].[BH4-].[Na+].CO>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 7730227Dimethyl 2,6-dichloroterephthalate

생성물 1

HCID 66712920Methyl 2,6-dichloro-4-(hydroxymethyl)benzoate수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of dimethyl 2,6-dichlorobenzene-1,4-dicarboxylate (2.3 g, 8.7 mmol) in tetrahydrofuran (10 mL) was treated with sodium borohydride (0.496 g, 13 mmol) and heated to refluxing temperature. The reaction mixture was then treated drop wise with methanol (1 mL) and continued refluxing for about 2 hours. The reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride solution followed by partitioning with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography using ethyl acetate in hexane (10%) as an eluant to yield methyl 2,6-dichloro-4-(hydroxymethyl)benzoate as a colorless liquid (1.6 g, 80%).

후처리

  1. temperatureheated
  2. temperatureto refluxing temperature
  3. temperaturecontinued refluxing for about 2 hours
  4. customquenched with saturated aqueous ammonium chloride solution
  5. customby partitioning with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0a80337fcf494295834c2681c507fd2a
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09364466B2

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