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

HRID 1735369Notes

Reaction equation

HRID 1735369 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 colorless 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 colorless liquid is obtained

Sources & evidence

ORD record
ord-bc8788262d0545a0b3ffe4ad9301da8c
Source dataset
uspto-grants-1996_07
Patent number
US05536442

Reaction notes

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