Water → HCID 178444372, compound

HRID 1583236Notes

Reaction equation

HRID 1583236 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:5]=[C:4]([F:19])[C:3]=1[N+]([O-])=O.[H][H].O.[CH:26]([OH:29])(C)C>O=[Pt]=O>[F:1][C:2]1[CH:7]=[C:6]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]2)[CH:5]=[C:4]([F:19])[C:3]=1[O:29][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 178418361HCID 178418361, compoundHCID 178444371HCID 178444371, compound

Product 1

HCID 178444372HCID 178444372, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

31.1 g of 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-nitrobenzene is dissolved in 450 ml of isopropanol and hydrogenated over 0.5 g of PtO2 at 20° and under normal pressure until the calculated quantity of hydrogen has been taken up. The solution is filtered and evaporated. The resulting crude, 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-aniline is dissolved in a mixture of 25 ml of concentrated sulfuric acid, 75 ml of dioxane and 75 ml of water and is diazotized at 3° to 6° with a solution of 8 g of NaNO2 in 15 ml of water. The mixture thus obtained is introduced in portions while stirring into 500 ml of boiling water. The mixture is boiled for a further 30 minutes and cooled and the resulting 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-phenol is filtered off and dissolved in 250 ml of 1N sodium hydroxide solution. 12.6 g of dimethyl sulfate is added in portions and the mixture is then heated at 100° for 1 hour. Cooling and working up in the usual manner gives 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-anisole.

Workup

  1. filtrationThe solution is filtered
  2. customevaporated
  3. dissolutionThe resulting crude, 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-aniline is dissolved in a mixture of 25 ml of concentrated sulfuric acid, 75 ml of dioxane and 75 ml of water
  4. customis diazotized at 3° to 6° with a solution of 8 g of NaNO2 in 15 ml of water
  5. customThe mixture thus obtained
  6. additionis introduced in portions
  7. temperaturecooled
  8. filtrationthe resulting 2,6-difluoro-4-(trans-4-pentylcyclohexyl)-phenol is filtered off
  9. dissolutiondissolved in 250 ml of 1N sodium hydroxide solution
  10. addition12.6 g of dimethyl sulfate is added in portions
  11. temperaturethe mixture is then heated at 100° for 1 hour
  12. temperatureCooling

Sources & evidence

ORD record
ord-d609b3d9e9664d62974842bed971638c
Source dataset
uspto-grants-1985_11
Patent number
US04551264

Reaction notes

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