Methanol → HCID 91421187, compound

HRID 1892874Notes

Reaction equation

HRID 1892874 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[C:18](=O)[CH:17]([CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO.S(=O)(=O)(O)O>C1(C)C=CC=CC=1.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[CH2:18][C:17]([CH2:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)=[CH:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 4311764Sodium borohydride2×HCID 58444090HCID 58444090, compound

Product 1

HCID 91421187HCID 91421187, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

82.3 g (229 mmole) 7-(4′-tert-Butyl-phenyl)-2-cyclohexylmethyl-indan-1-one were dissolved in 292 ml toluene in a 1 l—roundbottom flask equipped with a reflux condenser. 9.5 g (1.1 eq.) sodium borohydride were added. Then 40 ml (4.3 eq.) methanol were added at 50° C. and the mixture was stirred for 3 h at 50° C. An additional 1 g of sodium borohydride and 5 ml methanol were added and the mixture was stirred another 2 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. 350 ml of toluene. After addition of 0.7 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, evaporation of the solvent and crystallization from 800 ml ethanol afforded 67.3 g (86%) of the desired indene as white crystals. 1H-NMR (400 MHz, CDCl3): δ=7.45, 7.33, 7.25, 7.14 (4×m, 7H, aromatic), 6.69 (s, 1H, ═CH), 3.35 (s, 2H, benzylic), 2.34 (d, 2H, aliphatic), 1.71-1.50 (m, 6H, aliphatic), 1.39 (s, 9H, C(CH3)3), 1.24-0.87 (m, 5H, aliphatic) ppm.

Workup

  1. customequipped with a reflux condenser
  2. stirringthe mixture was stirred another 2 h at 50° C
  3. customwere separated
  4. washthe organic layer was washed two times with 2M sulphuric acid
  5. customThe solvent was evaporated
  6. dissolutionthe crude indanol was dissolved in approx. 350 ml of toluene
  7. additionAfter addition of 0.7 g p-toluene sulfonic acid the mixture
  8. temperaturewas heated
  9. temperatureto reflux
  10. customconversion (90 min)
  11. washThe solution was washed twice with a saturated NaHCO3-solution, once with water and once with a saturated sodium chloride solution
  12. dry with materialDrying over magnesium sulphate, evaporation of the solvent and crystallization from 800 ml ethanol

Sources & evidence

ORD record
ord-26f47d91923446eca285c32ae255557b
Source dataset
uspto-grants-2013_08
Patent number
US08507706B2

Reaction notes

Loading…