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

HRID 1070883Notes

Reaction equation

HRID 1070883 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 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).

Workup

  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%)

Sources & evidence

ORD record
ord-6531ad60005a499f898da23b03b00b0c
Source dataset
uspto-grants-2005_06
Patent number
US06903132B2

Reaction notes

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