Diethyl Ether → 8-Hydroxy-2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)dioxole

HRID 1450036ノート

反応式

HRID 1450036 の反応式
[CH3:1][C:2]1([CH3:16])[O:6][C:5]2[CH:7]=[C:8]3[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]3=[CH:15][C:4]=2[O:3]1.C([Li])CCC.C[Mg]Br.C([O:27]CC)C>>[OH:27][C:7]1[C:5]2[O:6][C:2]([CH3:16])([CH3:1])[O:3][C:4]=2[CH:15]=[C:9]2[C:8]=1[O:12][C:11]([CH3:14])([CH3:13])[O:10]2

参加物

5

反応物 4

HCID 3283Diethyl EtherHCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)HCID 178418339ButyllithiumHCID 178418573HCID 178418573、化合物

生成物 1

HCID 189431048-Hydroxy-2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)dioxole収率 28%

実験手順

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-(1,3)dioxole (5.00 g, 22.5 mmol (Example 5)) was dissolved in diethyl ether (150 mL, sodium benzophenone ketyl) under argon. n-Butyl lithium (10.0 mL, 25 mmol, 2.5M in toluene) was added at room temperature followed by methyl magnesium bromide (4.25 mL, 13 mmol, 3.0M in diethyl ether, Aldrich). the resulting mixture was stirred at room temperature for 1 h. Oxygen was bubbled through the solution over a period of 2 hours, while cooling with a cold water bath. The reaction mixture was poured into a solution of NaOH (50 mL, 1M) and extracted with diethyl ether (100 mL). The aqueous phase was acidified with conc. HCl to pH 2 while stirring. The product was isolated by extracting with diethyl ether (3×50 mL). The ether was dried (Na2SO4) and evaporated yielding 1.50 g (6.3 mmol, 28%) of 8-hydroxy-2,2,6,6-tetramethyl-benzo[1,2-d:4,5-d']bis(1,3)dioxole.

後処理

  1. customOxygen was bubbled through the solution over a period of 2 hours
  2. temperaturewhile cooling with a cold water bath
  3. additionThe reaction mixture was poured into a solution of NaOH (50 mL, 1M)
  4. extractionextracted with diethyl ether (100 mL)
  5. stirringwhile stirring
  6. customThe product was isolated
  7. extractionby extracting with diethyl ether (3×50 mL)
  8. dry with materialThe ether was dried (Na2SO4)
  9. customevaporated

出典と根拠

ORDレコード
ord-7f0d3860dc424566a821e7058f40b416
出典データセット
uspto-grants-1997_02
特許番号
US05599522

反応ノート

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