Sulfuric Acid → 3,3,6-Trimethyl-2,3-dihydro-1H-inden-5-ol

HRID 1070883ノート

反応式

HRID 1070883 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=O)[CH2:6][C:5]2([CH3:14])[CH3:13].S(=O)(=O)(O)O>CO>[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]([CH3:11])=[C:2]([OH:1])[CH:3]=2)[CH2:7][CH2:6]1

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 11701168HCID 11701168、化合物

生成物 1

HCID 30175493,3,6-Trimethyl-2,3-dihydro-1H-inden-5-ol収率 64%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Compound 135 was prepared by the catalytic hydrogenation (40 psi.) of 5-hydroxy-3,3,6-trimethyl-1-indanone (134) (1.54 g, 8.1 mmol) in methanol (13 mL) followed by the addition of sulfuric acid (169 μL). The content was degassed several times with nitrogen before palladium-on-charcoal (10%) was added. The hydrogenation was allowed to react overnight under hydrogen pressure. The reaction content was filtered through celite then brought to dryness. The residue was redissolved in diethyl ether, neutralized with sodium bicarbonate (10%) and washed with water and brine. 3,3,6-Trimethyl-5-indanol was purified with ethyl acetate and hexane (3%, 10% and 30%) to obtain 0.91 g of light yellow solid. (64% yield) Ref. Qd419-161, Wilt, J. W.; Schneider, C. A.; J. Org. Chem, 1961, 26, 4196. 1H NMR (300 MHz, CDCl3) δ 6 1.22 (s, 6H), 1.94 (dd, 2H, J=7.37, 6.99 Hz), 2.25 (s, 3H), 2.54 (s, 3H), 2.56 (s, 3H), 2.85 (d, 2H, J=7.18 Hz), 3.89 (s, 3H), 5.31 (d, 1H, J=3.59 Hz), 6.31 (s, 1H), 6.84 (s, 1H), 6.99 (bs, 1H), 7.07 (s, 1H), 7.16 (d, 1H, J=3.59 Hz), 8.33 (bs, 1H).

後処理

  1. customThe content was degassed several times with nitrogen before palladium-on-charcoal (10%)
  2. additionwas added
  3. customto react overnight under hydrogen pressure
  4. filtrationThe reaction content was filtered through celite
  5. dissolutionThe residue was redissolved in diethyl ether
  6. washwashed with water and brine
  7. custom3,3,6-Trimethyl-5-indanol was purified with ethyl acetate and hexane (3%, 10% and 30%)

出典と根拠

ORDレコード
ord-6531ad60005a499f898da23b03b00b0c
出典データセット
uspto-grants-2005_06
特許番号
US06903132B2

反応ノート

読み込み中…