Hydrogen Peroxide → (RS) 2-hydroxy-4-indanecarbonitrile

HRID 1646609

Reaction equation

HRID 1646609 reaction equation
CC(=C(C)C)C.[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:16]#[N:17])[CH2:9][CH2:8]1.[OH-].[Na+].OO.C([O:25]C(C)C)(C)C>O1CCCC1.O>[OH:25][CH:8]1[CH2:7][C:15]2[C:14]([C:16]#[N:17])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:9]1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 7914Diisopropyl EtherHCID 112502,3-Dimethyl-2-buteneHCID 14798Sodium HydroxideHCID 155761132,3-Dihydro-1H-indene-4-carbonitrile

Product 1

HCID 12857774(RS) 2-hydroxy-4-indanecarbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

42 ml of a 1M solution of boran-tetrahydrofuran complex is cooled to 0° C., 3.7 ml of 2,3-dimethyl-2-butene in 20 ml of tetrahydrofuran is added and agitation is carried out for one hour 15 minutes at 0° C. 1.98 g of product obtained in Stage A in 20 ml of tetrahydrofuran is introduced at 0° C. over 40 minutes, with agitation for 1/4 hour at 0° C., and the temperature is allowed to rise to +14° C. over 3 hours. After cooling to 0° C., 5 ml of water is added drop by drop with agitation for 5 minutes, then 18 ml of 2N sodium hydroxide is introduced at +2° C., and the temperature is allowed to rise to +15° C. 18 ml of hydrogen peroxide at 30% is added slowly and the mixture is left under agitation for 17 hours. The reaction mixture is poured into 100 ml of water and 100 ml of isopropyl ether and decanted; the aqueous phase is extracted with isopropyl ether. The reunited organic phases are washed with water, dried and concentrated to dryness under reduced pressure. The residue is chromatographed on silica in a hexane-ethyl acetate mixture (6-4), and 0.15 g of expected product is obtained, and 1.15 g of impure product is obtained which is chromatographed again on silica in a hexane-ethyl acetate mixture (65-35) so as to obtain 0.74 g of expected product, M.p.=60° C.

Workup

  1. waitto rise to +14° C. over 3 hours
  2. customto rise to +15° C
  3. waitthe mixture is left under agitation for 17 hours
  4. customdecanted
  5. extractionthe aqueous phase is extracted with isopropyl ether
  6. washThe reunited organic phases are washed with water
  7. customdried
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe residue is chromatographed on silica in a hexane-ethyl acetate mixture (6-4)

Sources & evidence

ORD record
ord-4ab0216b23454c2681ff253a1b1f5adf
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Linked notes

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