(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 1195472ノート

反応式

HRID 1195472 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-673068a0194047c58e76f7f6f95cdaee
出典データセット
uspto-grants-1992_05
特許番号
US05110955

反応ノート

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