Hexane → Methyl 4-acetyl-2,6-dichlorophenoxyacetate

HRID 743815

반응식

HRID 743815 반응식
[H-].[Na+].CCCCCC.[CH3:9][C:10]([C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([OH:19])=[C:14]([Cl:20])[CH:13]=1)=[O:11].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C.O>[C:10]([C:12]1[CH:13]=[C:14]([Cl:20])[C:15]([O:19][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[C:16]([Cl:18])[CH:17]=1)(=[O:11])[CH3:9]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 869201-(3,5-Dichloro-4-hydroxyphenyl)ethanone

생성물 1

HCID 18918381Methyl 4-acetyl-2,6-dichlorophenoxyacetate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (50% w/w dispersion in mineral oil, 1.32 g) was treated under argon with repeated washes of hexane. The oil-free residue was suspended in dry DMF (10 ml) and, with stirring and cooling (ice-bath), a solution of 3,5-dichloro-4-hydroxyacetophenone (5.13 g) in dry DMF (15 ml) was added dropwise. Stirring was continued for 30 minutes when methyl bromoacetate (3.06 ml) was added dropwise and stirring was continued for a further 18 hours at ambient temperature. The reaction mixture was added to water, the mixture was extracted twice with ethyl acetate, the organic phases dried (MgSO4), filtered and then evaporated. The residue, after recrystallisation from hexane (250 ml), gave methyl 4-acetyl-2,6-dichlorophenoxyacetate, 4.25 g, as white crystals: NMR (d6DMSO) δ8.00 (2H, s), 4.80 (2H, s), 3.73 (3H, s), 2.59 (3H, s).

후처리

  1. temperaturecooling (ice-bath)
  2. stirringStirring
  3. stirringstirring
  4. waitwas continued for a further 18 hours at ambient temperature
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. dry with materialthe organic phases dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue, after recrystallisation from hexane (250 ml)

출처 및 근거

ORD 기록
ord-b0149f6c7e52413f875b3b3e8c45e703
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556977

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