4-tert-Butylphenol → HCID 54348013, compound

HRID 1704086Notes

Reaction equation

HRID 1704086 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[C:23]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].[H-].[Na+].CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1>[CH3:6][O:5][C:3](=[O:4])[CH:2]([O:33][C:30]1[CH:31]=[CH:32][C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:28][CH:29]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 73934-tert-ButylphenolHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 54271297HCID 54271297, compound

Product 1

HCID 54348013HCID 54348013, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described in Example 3, 8.92 g of methyl bromo{p-[(p-chlorophenoxy)methoxy]phenyl}acetate, 3,45 g of p-tert.-butylphenol and 9.17 g of 60% sodium hydride-oil dispersion are reacted in 75 ml of tetrahydrofuran containing 1 ml of hexamethylphosphoramide and worked-up to give 11 g of product as an oil. Chromatography over silica gel with dichloromethane as eluent gives 7.1 g of gum which is crystallized from methanol to give 4.9 g of white crystals. Recrystallization gives white crystals, mp 64°-65° C.

Sources & evidence

ORD record
ord-f75d62e213724a379b528c7cf5ccf794
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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