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

HRID 1070885노트

반응식

HRID 1070885 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 carried out overnight under hydrogen pressure. The reaction was fileterd and the solvents evaportated. The residue was dissolved in diethyl ether, neutralized with sodium bicarbonate (10%) and washed with water and brine. 3,3,6-Trimethyl-5-indanol was purified by column chromatography using 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 6.93 (s, 1H), 6.56 (s, 1H), 2.78 (t, 2H), 2.20 (s, 3H), 1.89 (t, 2H) and 1.21 (s, 6H). GCMS 176 at 7.91 retention time. Compound 160 is

후처리

  1. customThe content was degassed several times with nitrogen before palladium-on-charcoal (10%)
  2. additionwas added
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed with water and brine
  5. custom3,3,6-Trimethyl-5-indanol was purified by column chromatography

출처 및 근거

ORD 기록
ord-4b8f726d235445f6ba2deee80c97c63e
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903132B2

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