Methanol → HCID 90793975, compound

HRID 2070686Notes

Reaction equation

HRID 2070686 reaction equation
[C:1]1([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)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].CO.S(=O)(=O)(O)O>C1(C)C=CC=CC=1.O>[C:1]1([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)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 59545165HCID 59545165, compound

Product 1

HCID 90793975HCID 90793975, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

24 g (68 mmole) 7-(1-Naphthyl)-2-cyclohexylmethyl-indan-1-one were dissolved in 85 ml toluene in a 500 ml-roundbottom flask equipped with a reflux condenser. 2.82 g (1.1 eq.) sodium borohydride were added. Then 11.8 ml (4.3 eq.) methanol were added at 50° C. and the mixture was stirred for 5 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. 250 ml of toluene. After addition of 0.5 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 21.65 g (95%) of the desired indene as a slightly offwhite oil. 1H-NMR (400 MHz, CDCl3): δ=7.88 (m, 2H, aromatic), 7.73 (d, 1H, aromatic), 7.55-7.19 (m, 7H, aromatic), 6.10 (s, 1H, C═CH), 3.40 (s, 2H, benzylic) 2.25 (d, 2H CH2Cy), 1.67-0.80 (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. 250 ml of toluene
  6. additionAfter addition of 0.5 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-34348be08f3a4f27940b715f5a92e70c
Source dataset
uspto-grants-2012_10
Patent number
US08299287B2

Reaction notes

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