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

HRID 1070883노트

반응식

HRID 1070883 반응식
[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

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 11701168HCID 11701168, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-6531ad60005a499f898da23b03b00b0c
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903132B2

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