Sodium Dithionite → (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate

HRID 1195473ノート

反応式

HRID 1195473 の反応式
[C:1]([O:9][CH2:10]/[CH:11]=[C:12](\[CH3:26])/[CH2:13][CH2:14][C:15]1[C:20](=[O:21])[C:19]([CH3:22])=[C:18]([CH3:23])[C:17](=[O:24])[C:16]=1[CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:9][CH2:10]/[CH:11]=[C:12](\[CH3:26])/[CH2:13][CH2:14][C:15]1[C:16]([CH3:25])=[C:17]([OH:24])[C:18]([CH3:23])=[C:19]([CH3:22])[C:20]=1[OH:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 24489Sodium DithioniteHCID 67900681(E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate

生成物 1

HCID 86745748(E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate収率 84.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1.22 g (3.5 mmol) of (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate in 10 ml of THF was treated dropwise with a solution of 0.9 g of sodium dithionite in 8 ml of water. After 1 hour the mixture was extracted with chloroform (2 x) and the combined extracts were washed three times with water. The residue remaining after removal of the solvent was washed with hexane and dried under vacuum, yielding 1.05 g of colourless (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate. M.P. 112°-114° C.

後処理

  1. extractionAfter 1 hour the mixture was extracted with chloroform (2 x)
  2. washthe combined extracts were washed three times with water
  3. customafter removal of the solvent
  4. washwas washed with hexane
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-ad3e34a8875d45adb1cadf8d3c54d752
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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