(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate → (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate

HRID 1195472노트

반응식

HRID 1195472 반응식
[C:1]([O:9][CH2:10]/[CH:11]=[C:12](\[CH3:28])/[CH2:13][CH2:14][C:15]1[C:20]([CH3:21])=[C:19]([O:22]C)[C:18]([CH3:24])=[C:17]([CH3:25])[C:16]=1[O:26]C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O.C(#N)C>[C:1]([O:9][CH2:10]/[CH:11]=[C:12](\[CH3:28])/[CH2:13][CH2:14][C:15]1[C:16](=[O:26])[C:17]([CH3:25])=[C:18]([CH3:24])[C:19](=[O:22])[C:20]=1[CH3:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 86745747(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate

생성물 1

HCID 67900681(E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate수율 73.7%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

A solution of ceric ammonium nitrate (7.2 g; 13.1 mmol) in water (30 ml) was added dropwise while cooling with ice to a solution of (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate (2 g; 5.2 mmol) in acetonitrile (30 ml). After completion of the addition the mixture was diluted with water and extracted with chloroform. The extracts were washed with water, dried and freed from solvent. The residue crystallizes spontaneously and 1.35 g of (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate was obtained. M.P, 74.5°-75.5° C.

후처리

  1. additionAfter completion of the addition the mixture
  2. extractionextracted with chloroform
  3. washThe extracts were washed with water
  4. customdried
  5. customThe residue crystallizes spontaneously

출처 및 근거

ORD 기록
ord-673068a0194047c58e76f7f6f95cdaee
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110955

반응 노트

불러오는 중…