4-Chloro-3-methylphenol → HCID 131711334, compound

HRID 1704106Notes

Reaction equation

HRID 1704106 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[H-].[Na+].[I-].[K+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH3:19][O:18][C:16](=[O:17])[CH:15]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH3:9])[CH:4]=1)[C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 17324-Chloro-3-methylphenolHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 22761172HCID 22761172, compound

Product 1

HCID 131711334HCID 131711334, compoundYield 105.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

As described in Example 30, a mixture of 2.86 g of 4-chloro-3-methylphenol, 0.80 g of 60% sodium hydride-oil dispersion, 3.32 g of potassium iodide, one ml of hexamethylphosphoramide and 8.52 g of methyl bromo{p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate in 70 ml of tetrahydrofuran is refluxed for 18 hours and worked-up to give 10.1 g of gum. The gum is crystallized from petroleum ether containing a small amount of ether to give 7.7 g of white crystals. Purification by chromatography over silica gel with dichloromethane and recrystallization from petroleum ether-ether and benzene-hexane gives crystals, mp 74°-76° C.

Workup

  1. temperatureis refluxed for 18 hours

Sources & evidence

ORD record
ord-324efc5f34f24a6abf350b28fe7c0c8e
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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