4-Chlorophenol → HCID 54549334, compound

HRID 1704085Notes

Reaction equation

HRID 1704085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[I-].[K+].Br[CH:14]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16]>O1CCCC1.C(O)(=O)C.O.CN(C)P(N(C)C)(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:14]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][O:27][C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)=[CH:23][CH:24]=2)[C:15]([O:17][CH3:18])=[O:16])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 46844-ChlorophenolHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 54271297HCID 54271297, compound

Product 1

HCID 54549334HCID 54549334, compoundYield 103.4%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of 2.74 g of p-chlorophenol in 25 ml of tetrahydrofuran is added 0.85 g of 60% sodium hydride-oil dispersion. After stirring under argon at room temperature for 1 hour, 3.52 g of potassium iodide and 1 ml of hexamethylphosphoramide is added. To the mixture is added dropwise, a solution of 8.18 g of methyl bromo{p-[(p-chlorophenoxy)methoxy]phenyl}acetate in 45 ml of tetrahydrofuran. The mixture is refluxed for 18 hours. The mixture is poured into 500 ml of ice and water containing 2 ml of acetic acid. The mixture is extracted with ether and the ether extracts are washed with sodium chloride solution, sodium bicarbonate solution and with sodium chloride solution. The extract is dried (MgSO4) and the solvent removed under reduced pressure to give the product (9.5 g) as a viscous oil. Chromatography over silica gel with dichloromethane as eluent gives 7.6 g of gum which is crystallized from methanol to give 5.8 g of the product as white crystals. Recrystallization from methanol gives white crystals, mp 64°-65° C.

Workup

  1. additionTo the mixture is added dropwise
  2. temperatureThe mixture is refluxed for 18 hours
  3. extractionThe mixture is extracted with ether
  4. washthe ether extracts are washed with sodium chloride solution, sodium bicarbonate solution and with sodium chloride solution
  5. dry with materialThe extract is dried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4d9bde4fab2a45a692981d8a91108336
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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