4-Chlorophenol → HCID 131711328, compound

HRID 1704094Notes

Reaction equation

HRID 1704094 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][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16]>O1CCCC1>[CH3:18][O:17][C:15](=[O:16])[CH:14]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 54245390HCID 54245390, compound

Product 1

HCID 131711328HCID 131711328, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in Example 5, a mixture of 2.52 g of p-chlorophenol, 0.785 g of 60% sodium hydride-oil dispersion, 3.60 g of potassium iodide and 7.8 g of methyl bromo{p-[2-(p-chlorophenoxy)ethoxy]phenyl}acetate in 70 ml of tetrahydrofuran are refluxed for 18 hours and worked up to give 8.6 g of oil. The oil is triturated with hexane to give 6.9 g of tan crystals. Two recrystallizations from methanol gives the product as white crystals, mp 97°-112° C.

Workup

  1. temperatureare refluxed for 18 hours

Sources & evidence

ORD record
ord-c4d4996487474975b79c769b8fa70464
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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