Chlorodifluoromethane → 4-Difluoromethoxy-4'-octoxy-biphenyl

HRID 274159Notes

Reaction equation

HRID 274159 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH:26]([F:28])[F:27]>O.O1CCOCC1>[F:27][CH:26]([F:28])[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 104943294-Hydroxy-4'-octyloxybiphenyl

Product 1

HCID 147659684-Difluoromethoxy-4'-octoxy-biphenyl

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 20 g of 4-hydroxy-4'-octyloxybiphenyl, 13.6 g of NaOH, 100 ml of water and 150 ml of dioxane is heated to 70° C. with stirring. 10 g of chlorodifluoromethane are passed into the cooled two-phase mixture with vigorous stirring. The reaction mixture is poured into water, and the product is extracted with petroleum ether. The organic phase is dried over Na2SO4, evaporated, and the residue is filtered through a short silica gel column using petroleum ether as eluent. The product is recrystallized from acetonitrile. Colourless crystals are obtained. m.p.: 104° C., c.p.: 20° C. (extrapolated), Δn =0.093, viscosity: 17

Workup

  1. extractionthe product is extracted with petroleum ether
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customevaporated
  4. filtrationthe residue is filtered through a short silica gel column
  5. customThe product is recrystallized from acetonitrile
  6. customColourless crystals are obtained
  7. custom20° C. (extrapolated), Δn =0.093, viscosity

Sources & evidence

ORD record
ord-fec369f2816e47d4a947b4b8308e08c5
Source dataset
uspto-grants-1995_02
Patent number
US05389292

Reaction notes

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