Ammonia → HCID 178444420, compound

HRID 246788Notes

Reaction equation

HRID 246788 reaction equation
N.[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:16]2)=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH3:5].[Li].C(O)C>C(OCC)C>[CH2:2]([O:6][C:7]1[CH2:12][CH:11]=[C:10]([CH2:13][CH2:14][C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:16]2)[CH2:9][CH:8]=1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 702EthanolHCID 3028194LithiumHCID 178444421HCID 178444421, compound

Product 1

HCID 178444420HCID 178444420, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
10 °C

Procedure

1306 ml of liquid ammonia were placed in a sulphonation flask and then a solution of 38.4 g of 4-butyloxy-1-[2-(trans-4-pentylcyclohexyl)ethyl]benzene in 1.1 l of diethyl ether was added dropwise within 40 minutes while cooling. 23.3 g of lithium wire were subsequently added within 35 minutes and the mixture was stirred for 2 hours. 420 ml of ethanol were then added dropwise to the mixture within 70 minutes and the ammonia was allowed to evaporate overnight under nitrogen. The mixture was cooled to 10° C. and 1.5 l of water were then added dropwise within 35 minutes in such a manner that the temperature did not rise above 10° C. The mixture was extracted three times with 0.5 l of diethyl ether each time. The organic phases were washed twice with 0.5 l of water each time, dried over potassium carbonate, filtered and concentrated, there being obtained 39.0 g of 4-butyloxy-1-[2-(trans-4-pentylcyclohexyl)ethyl]-1,4-cyclohexadiene as a colourless crystallizing oil.

Workup

  1. temperaturewhile cooling
  2. customto evaporate overnight under nitrogen
  3. addition1.5 l of water were then added dropwise within 35 minutes in such a manner that the temperature
  4. customdid not rise above 10° C
  5. extractionThe mixture was extracted three times with 0.5 l of diethyl ether each time
  6. washThe organic phases were washed twice with 0.5 l of water each time
  7. dry with materialdried over potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6f114494ed1f450eb069c4154ad362bf
Source dataset
uspto-grants-1987_11
Patent number
US04704005

Reaction notes

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