HCID 19901492, compound → 4-Decyl-4'-methoxy-1,1'-biphenyl

HRID 2372674Notes

Reaction equation

HRID 2372674 reaction equation
C(C(O[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=O)CCCCCCCC.[H][H]>[C].[Pd].C(O)(=O)C>[CH2:17]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)=[CH:17][CH:18]=1)[CH2:18][CH2:13][CH2:14][CH2:15][CH2:16][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 19901492HCID 19901492, compound2×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 199014874-Decyl-4'-methoxy-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 38 g of 4-phenylphenol, 9 g of sodium hydroxide, 200 ml of methanol and 20 ml of water was heated. 28 g of dimethyl sulfate was dropped in the mixture with stirring at 50° C. After one hour, 20 ml of 10N-sodium hydroxide was dropped in the solution and continued stirring for 2 hours. The crystals were obtained after the solution was cooled to room temperature. After washing with water and methanol for several times, 30 g of 4-methoxybiphenyl (O) was obtained. 154 g of (O) was dissolved with mixed solution of 200 ml of chloroform and 75 ml of carbon tetrachloride, and then 11 g of aluminum chloride powder was added to the solution. 14 g of octanic acid chloride was added to the solution with stirring after changing colour of the solution to greenish blue. 150 ml of ice-water and 5 ml of conc. hydrochloric acid was added, after refluxing 5 hours. The water layer was removed, then the organic layer was washed with 0.1N hydrochloric acid and dehydrated with magnesium sulfate anhydride, and then evaporated after filtration to obtain crude crystals of 4'-nonylcarbonyloxy-4-methoxybiphenyl (P). 13 g of (P), 1 g of 10% palladium-carbon, 130 ml of acetic acid were put into an autoclave and then gave the pressure to 25 kg/cm2 by using hydrogen. (P) was reduced by heating for 3 hours at 80° C. After substituting nitrogen for hydrogen, palladium-carbon was separated by filtrating the reacted solution. 4'-decyl-4-methoxybiphenyl (Q) was obtained after cooling and drying. 8 g of (Q), 90 ml of acetic acid 30 ml of hydrogen bromide water solution were mixed and refluxed for 5 hours to obtain crude crystals. After cooling, the crude crystals were washed with methanol to crystallize 5.5 g of 4-(4'-octylphenyl)phenol.

Workup

  1. customgave the pressure to 25 kg/cm2
  2. customwas separated
  3. filtrationby filtrating the reacted solution

Sources & evidence

ORD record
ord-2a460d9449d6439a806ccd55f709f9ab
Source dataset
uspto-grants-1992_03
Patent number
US05100579

Reaction notes

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