Sulfuric Acid → HCID 18433875, compound

HRID 2305947Notes

Reaction equation

HRID 2305947 reaction equation
[CH:1]1([C:6](O)([CH3:12])[CH2:7][CH2:8][CH2:9][C:10]#[N:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.C1(C(C)CCCC#N)CCCC=1>C(O)(=O)C.CC(OC)(C)C>[C:1]1(=[C:6]([CH3:12])[CH2:7][CH2:8][CH2:9][C:10]#[N:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 18433859HCID 18433859, compoundHCID 18433865HCID 18433865, compound

Product 1

HCID 18433875HCID 18433875, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
5 °C

Procedure

Crude 5-cyclopentyl-5-hydroxyhexanenitrile (18 g; 0.1 mol) from example 13(a) was added into a solution of sulphuric acid (15 ml) in acetic acid (150 ml). The reaction mixture was stirred at 5° C. for 1 hour, then poured into ice (100 g), diluted with MTBE (100 ml), washed with saturated sodium bicarbonate solution (5×300 ml) and brine (2×300 ml), dried (MgSO4), concentrated in vacuo, and bulb-to-bulb distilled to give 2.1 g (13% yield) of 5-cyclopentylidene-hexanenitrile and 5-(cyclopent-1-enyl)-hexanenitrile mixture (GC: 43+57%).

Workup

  1. washwashed with saturated sodium bicarbonate solution (5×300 ml) and brine (2×300 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo, and bulb-to-bulb
  4. distillationdistilled

Sources & evidence

ORD record
ord-fb490cc2b90f4ffba87f8c1b8e2b0000
Source dataset
uspto-grants-2002_08
Patent number
US06441052B1

Reaction notes

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