Methanol → HCID 91509317, compound

HRID 2070690Notes

Reaction equation

HRID 2070690 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:17]=2[C:16](=O)[C:15]([CH3:25])(C2CCCCC2)[CH2:14]3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[BH4-].[Na+].CO.S(=O)(=O)(O)O>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:17]=2[CH2:16][C:15]([CH2:25][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)=[CH:14]3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 86646802HCID 86646802, compound

Product 1

HCID 91509317HCID 91509317, compoundYield 183.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

25.3 g (76.1 mmole) 7-(3′,5′-Dimethylphenyl)-2-cyclohexyl-methyl-indan-1-one were dissolved in 90 ml toluene in a 500 ml-roundbottom flask equipped with a reflux condenser. 3.17 g (1.1 eq.) sodium borohydride were added. Then 13.3 ml (4.35 eq.) methanol were added at 50° C. and the mixture was stirred for 3 h at 50° C. 2M sulphuric acid was added until the gas evolution ceased. After addition of 100 ml water the layers were separated and the organic layer was washed two times with 2M sulphuric acid and once with a saturated sodium chloride solution. The solvent was evaporated and the crude indanol was dissolved in approx. 90 ml of toluene. After addition of 0.3 g p-toluene sulfonic acid the mixture was heated to reflux using a Dean-Stark-trap until TLC showed complete conversion (90 min). The solution was washed twice with a saturated NaHCO3-solution, once with water and once with a saturated sodium chloride solution. Drying over magnesium sulphate and evaporation of the solvent afforded 22.1 g (92%) of the desired indene as a slightly offwhite oil. 1H-NMR (400 MHz, CDCl3): δ=7.35 (d, 1H, aromatic), 7.24 (m, 1H, aromatic), 7.15 (m, 3H, aromatic), 7.01 (s, 1H, aromatic), 6.68 (s, 1H, C═CH), 3.37 (s, 2H, benzylic), 2.39 (s, 6H, PhCH3), 2.36 (d, 2H, CH2Cy), 1.74-0.91 (m, 11H, aliphatic) ppm.

Workup

  1. customequipped with a reflux condenser
  2. customwere separated
  3. washthe organic layer was washed two times with 2M sulphuric acid
  4. customThe solvent was evaporated
  5. dissolutionthe crude indanol was dissolved in approx. 90 ml of toluene
  6. additionAfter addition of 0.3 g p-toluene sulfonic acid the mixture
  7. temperaturewas heated
  8. temperatureto reflux
  9. customconversion (90 min)
  10. washThe solution was washed twice with a saturated NaHCO3-solution, once with water and once with a saturated sodium chloride solution
  11. dry with materialDrying over magnesium sulphate and evaporation of the solvent

Sources & evidence

ORD record
ord-5a02eb4e69144b399de9996481716af4
Source dataset
uspto-grants-2012_10
Patent number
US08299287B2

Reaction notes

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