Water → HCID 178444327, compound

HRID 247674Notes

Reaction equation

HRID 247674 reaction equation
Br[CH:2]([CH:18](Br)[CH2:19][CH3:20])[CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.O>C(O)(=O)C.[Zn]>[CH:3](/[C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)=[CH:2]\[CH2:18][CH2:19][CH3:20].[CH:3](/[C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)=[CH:2]/[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 2

HCID 962WaterHCID 178438277HCID 178438277, compound

Product 2

HCID 178444327HCID 178444327, compoundYield 48%HCID 178444328HCID 178444328, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1.98 g of p-[trans-4-(2,3-dibromopentyl)cyclohexyl]benzonitrile (erythro/threo 66.6:32.8) in 30 ml of glacial acetic acid was treated at room temperature with 2.0 g of zinc powder while gassing with argon and the suspension was stirred at room temperature for 1 hour. The reaction mixture was subsequently poured into 100 ml of water and extracted three times with 100 ml of petroleum ether each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the yellowish residue (1.16 g) on silver nitrate-coated silica gel with hexane/diethyl ether (vol. 90:10) gave 586 mg (48%) of p-[trans-4-(2E-pentenyl)cyclohexyl]benzonitrile and 171 mg (14%) of p-[trans-4-(2Z-pentenyl)cyclohexyl]benzonitrile as colourless oils. The 2E-isomer has a melting point of 9.6° C. and 16.1° C. (2 modifications) and a virtual clearing point of -67° C.; the 2Z-isomer has a melting point of -7.7° C. and a virtual clearing point of -54° C.

Workup

  1. extractionextracted three times with 100 ml of petroleum ether each time
  2. washThe organic phases were washed twice with 100 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-894b4502453c4d80ab50e89cda2790c7
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Reaction notes

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