Hydrochloric Acid → (2,5-Dimethoxy-4-methylphenyl)-7,7-dimethyloctan-1-one

HRID 844427

반응식

HRID 844427 반응식
[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O.C(Cl)(=O)C(Cl)=O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[CH3:29].[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl.CN(C=O)C>[CH3:28][O:27][C:24]1[CH:23]=[C:22]([CH3:29])[C:21]([O:20][CH3:19])=[CH:26][C:25]=1[C:8](=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([CH3:1])([CH3:12])[CH3:11]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 62838Versatic 10HCID 65578Oxalyl chlorideHCID 905522,5-DimethoxytolueneHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 22612534(2,5-Dimethoxy-4-methylphenyl)-7,7-dimethyloctan-1-one

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

1 g of 7,7-dimethyloctanoic acid is dissolved in 20 ml of DCM cooled to 0° C., 0.57 ml of oxalyl chloride is added and the mixture is then left stirring for 1 hour at 0° C. and for 2 hours at RT. 0.93 ml of 2,5-dimethoxytoluene and one drop of DMF are added, the mixture is cooled to 0° C., 940 mg of AlCl3 are then added and the mixture is left stirring for 1 hour at 0° C. and overnight at RT. It is poured into 10% HCl solution and extracted with ether, and the combined organic phases are then washed with 2N sodium hydroxide, dried and concentrated. The residue is chromatographed on silica, eluting with DCM/pentane (85/15; v/v) to give 1.05 g of the expected compound.

후처리

  1. waitthe mixture is then left
  2. temperaturethe mixture is cooled to 0° C.
  3. waitthe mixture is left
  4. stirringstirring for 1 hour at 0° C. and overnight at RT
  5. extractionextracted with ether
  6. washthe combined organic phases are then washed with 2N sodium hydroxide
  7. customdried
  8. concentrationconcentrated
  9. customThe residue is chromatographed on silica
  10. washeluting with DCM/pentane (85/15; v/v)

출처 및 근거

ORD 기록
ord-60fc8cae1c7841cdb0b8184243239d20
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380230B1

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