Dimethylformamide → 1,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene

HRID 894426Notes

Reaction equation

HRID 894426 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1O.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].CN(C)C=O>CCOCC.CCCCC>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([O:6][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[O:21][CH2:18][C:2]1[CH:8]=[CH:7][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 811054-Bromoresorcinol

Product 1

HCID 128821681,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzeneYield 30%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

A mixture of 75.0 g. (0.397 mol.) of 4-bromoresorcinol, 95.1 ml. (0.80 mol.) of benzylbromide and 331 g. (2.4 mol.) of anhydrous potassium carbonate in 400 ml. of N,N-dimethylformamide is stirred for 12 hours at 25° C. and for 4 hour at 85° C. The reaction mixture is cooled and added to one liter of ice-200 ml. pentane-100 ml. ether. The organic phase is washed with three 500 ml. portions of water, dried over magnesium sulfate and evaporated to an oil. The oil is rapidly chromatographed on 400 g. of silica gel eluted with 20% ether-pentane to yield 80 g. of oil. The chromatographed oil is crystallized from pentane at 0° C. to yield 45.0 g. (30%) of the title compound, M.P. 37°-38° C.

Workup

  1. additionA mixture of 75.0 g
  2. temperatureThe reaction mixture is cooled
  3. washThe organic phase is washed with three 500 ml
  4. dry with materialportions of water, dried over magnesium sulfate
  5. customevaporated to an oil
  6. customThe oil is rapidly chromatographed on 400 g
  7. washof silica gel eluted with 20% ether-pentane
  8. customto yield 80 g
  9. customThe chromatographed oil is crystallized from pentane at 0° C.
  10. customto yield 45.0 g

Sources & evidence

ORD record
ord-24f4fc226fa94b2885ca541b54e4664e
Source dataset
uspto-grants-1981_08
Patent number
US04283569

Reaction notes

Loading…