Chlorodifluoromethane → 1-(Benzyloxy)-4-(difluoromethoxy)benzene

HRID 274161Notes

Reaction equation

HRID 274161 reaction equation
C1(C(C2[C:14]([CH2:15][O:16][CH2:17][C:18]3[C:23](C4C(=CC=C(O)C=4)O)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)=CC(=CC=1)O)O.[OH-:32].[Na+].Cl[CH:35]([F:37])[F:36]>O.O1CCOCC1>[CH2:17]([O:16][C:15]1[CH:10]=[CH:11][C:12]([O:32][CH:35]([F:37])[F:36])=[CH:13][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 132534121-(Benzyloxy)-4-(difluoromethoxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 40.0 g of hydroquinone monobenzyl ether, 40 g of NaOH, 200 ml of water and 300 ml of dioxane are heated to 70° C. with stirring. 35.5 g of chlorodifluoromethane are passed into the cooled 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 chromatographed through a short silica gel column, using petroleum ether/ethyl acetate 8:2 as eluent. A colourless liquid is obtained.

Workup

  1. extractionthe product is extracted with petroleum ether
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customevaporated
  4. customthe residue is chromatographed through a short silica gel column
  5. customA colourless liquid is obtained

Sources & evidence

ORD record
ord-7520cfc2627e45bcb015516c349ce02e
Source dataset
uspto-grants-1995_02
Patent number
US05389292

Reaction notes

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