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

HRID 1070885Notes

Reaction equation

HRID 1070885 reaction equation
[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

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 11701168HCID 11701168, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-4b8f726d235445f6ba2deee80c97c63e
Source dataset
uspto-grants-2005_06
Patent number
US06903132B2

Reaction notes

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