Sulfuric Acid → HCID 18433870, compound

HRID 2187321Notes

Reaction equation

HRID 2187321 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.[CH:17]1([CH:22]([CH3:28])[CH2:23][CH2:24][CH2:25][C:26]#N)[CH2:21][CH2:20][CH2:19][CH2:18]1.[OH:29]S(O)(=O)=O>CC(OC)(C)C.CO>[CH:17]1([CH:22]([CH3:28])[CH2:23][CH2:24][CH2:25][CH:26]=[O:29])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8058HexaneHCID 18433853HCID 18433853, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18433870HCID 18433870, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
-70 °C

Procedure

Diisobutylaluminum hydride (60 ml of 1.0 M solution in hexane) was added at −65° C. to a hexane (50 ml) solution of 5-cyclopentylhexanenitrile (5.0 g; 30 mmol; from example 11). After stirring at −70° C. for 0.5 hour, and at room temperature for 3 hours, methanol (1.8 ml) was added, and the stirring continued for 20 minutes. 10% H2SO4 (48 ml) was added, and the reaction mixture was diluted with MTBE (150 ml). The organic layer was separated, washed with saturated sodium bicarbonate solution (300 ml) and brine (3×300 ml), dried (MgSO4), concentrated in vacuo, and bulb-to-bulb distilled (100° C./0.2 torr) to give 2.6 g (51.5% yield) of 5-cyclopentylhexanal.

Workup

  1. waitat room temperature for 3 hours
  2. waitthe stirring continued for 20 minutes
  3. customThe organic layer was separated
  4. washwashed with saturated sodium bicarbonate solution (300 ml) and brine (3×300 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo, and bulb-to-bulb
  7. distillationdistilled (100° C./0.2 torr)

Sources & evidence

ORD record
ord-843d851fa0ce41aca16d22d321de8b39
Source dataset
uspto-grants-2002_06
Patent number
US06410000B1

Reaction notes

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