Potassium Carbonate → 4-(4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethyl-1-nitrobenzene

HRID 2295792

Reaction equation

HRID 2295792 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[Cl:13][C:14]1[C:23]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=2[C:17]([OH:24])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:13][C:14]1[C:23]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=2[C:17]([O:24][C:2]2[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=2[CH3:12])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzeneHCID 202033334-Chloro-5,6,7,8-tetrahydronaphthalen-1-ol

Product 1

HCID 132459914-(4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethyl-1-nitrobenzeneYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 35.62 g (0.19 mole) of 4-chloro-3,5-dimethyl-1-nitrobenzene and 38.54 g (0.21 mole) of 4-chloro-5,6,7,8-tetrahydro-1-naphthol in 300 mL of dry DMF under an atmosphere of nitrogen and at room temperature was added 29.16 g (0.21 mole) of anhydrous potassium carbonate. The resulting reaction mixture was heated to 140° C. (internal). The reaction mixture was then heated between 140° and 150° C. for 40 hrs. The reaction mixture was then cooled to room temperature. The DMF was removed on a rotary evaporator in vacuo. The remaining dark brown semi-solid was dissolved in 500 mL of hot toluene and filtered. The collected solids were thoroughly washed with hot toluene. The toluene washings were combined with the toluene filtrate and the solvents removed to afford 34.8 g of dark brown solid. Recrystallization from hot hexane containing a little ethylene acetate along with the use of decolorizing carbon afforded 22.04 g of pale yellow solid; m.p. 176° -179° C. NMR (CDCl3): δ1.7-2.0 (m, 4H), 2.20 (S, 6H), 2.7-3.0 (m, 4H), 5.95 (d, J=9 Hz, 1H), 6.95 (d, J=9 Hz, 1H), 8.02 (S, 2H).

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was then heated between 140° and 150° C. for 40 hrs
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. customThe DMF was removed on a rotary evaporator in vacuo
  5. dissolutionThe remaining dark brown semi-solid was dissolved in 500 mL of hot toluene
  6. filtrationfiltered
  7. washThe collected solids were thoroughly washed with hot toluene
  8. customthe solvents removed

Sources & evidence

ORD record
ord-26d000774968408f832523a640a25cf0
Source dataset
uspto-grants-1984_01
Patent number
US04426385

Linked notes

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