Acetic Acid → Phytyltrimethylhydroquinone

HRID 48197

反応式

HRID 48197 の反応式
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].[CH3:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH2:20][CH2:21][CH2:22][CH:23]([CH2:25][CH2:26][CH2:27][C:28](O)([CH:30]=C)[CH3:29])[CH3:24])[CH3:19])[CH3:14].[C:33](O)(=O)C>CCOCC.CO.[Cl-].[Zn+2].[Cl-]>[CH2:1]([C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([OH:7])[C:8]=1[CH3:33])/[CH:12]=[C:13](/[CH2:15][CH2:16][CH2:17][C@@H:18]([CH2:20][CH2:21][CH2:22][C@@H:23]([CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH3:24])[CH3:19])\[CH3:14]

参加物

7

反応物 3

HCID 176Acetic AcidHCID 10453IsophytolHCID 12785Trimethylhydroquinone

生成物 1

HCID 87503419Phytyltrimethylhydroquinone収率 47%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

The solution of trimethylhydroquinone (30, 7.5 g, 49.28 mmol), isophytol (12 g, 40.47 mmol), anhydrous zinc chloride (3 g, 22.01 mmol) and 0.4 mL of glacial acetic acid in 60 mL of absolute ether was refluxed for 1 h. The solvent was then removed in vacuo at 50° C. and the slurry obtained was dissolved in a mixture of 50 mL of petroleum ether and 20 mL of 70% aqueous methanol. The emulsion formed was destroyed by the addition of 20 mL of ether. The ether layer was dried (Na2SO4) and evaporated in vacuo to give a red solid paste that was triturated vigorously with 70 mL of petroleum ether. After cooling to −78° C., the suspension was centrifuged and the supernatant petroleum ether was decanted. Cold petroleum ether (10 mL) was added to the crystalline mass, and the operation was twice repeated to give 10 g (47%) of sticky white solid, which was used in the next step without further purification.

後処理

  1. customThe solvent was then removed in vacuo at 50° C.
  2. customthe slurry obtained
  3. customThe emulsion formed
  4. customwas destroyed by the addition of 20 mL of ether
  5. dry with materialThe ether layer was dried (Na2SO4)
  6. customevaporated in vacuo
  7. customto give a red solid paste that
  8. customwas triturated vigorously with 70 mL of petroleum ether
  9. customthe supernatant petroleum ether was decanted
  10. additionCold petroleum ether (10 mL) was added to the crystalline mass

出典と根拠

ORDレコード
ord-dc07e42ebc2e4eedb1b3fa31aec964ab
出典データセット
uspto-grants-2004_03
特許番号
US06703384B2

関連ノート

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