4-tert-Butylphenol → HCID 12531881, compound

HRID 1863331Notes

Reaction equation

HRID 1863331 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CN(C)P(N(C)C)(N(C)C)=O.Br[CH:26]([C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=2)=[CH:33][CH:32]=1)[C:27]([O:29][CH3:30])=[O:28]>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:26]([C:31]2[CH:32]=[CH:33][C:34]([O:37][C:38]3[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=3)=[CH:35][CH:36]=2)[C:27]([O:29][CH3:30])=[O:28])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 73934-tert-ButylphenolHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 20392570HCID 20392570, compound

Product 1

HCID 12531881HCID 12531881, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3.75 g of 4-t-butylphenol in 40 ml of tetrahydrofuran was added 0.88 g of sodium hydride (oil dispersion). After stirring 30 minutes, 1 ml of hexamethylphosphoramide was added and a solution of 7.36 g of methyl α-bromo-α-[p-(p-nitrophenoxy)phenyl]acetate in 25 ml of tetrahydrofuran was added over a period of 30 minutes. The mixture was stirred at room temperature for 30 minutes and refluxed for 30 minutes. The mixture was poured into 130 ml of ice-water and extracted with dichloromethane. The extracts were washed with saturated sodium chloride solution and chilled. Filtration gave 2.1 g of product. The filtrate was concentrated to an oil under vacuum and chromatographed over silica gel (eluent-CCl4). From the first fractions there was obtained 4.3 g of solid which was dissolved in hot methanol and the volume reduced. Chilling gave 3.7 g of product as pale yellow crystals, mp 101°-103° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. temperaturerefluxed for 30 minutes
  3. extractionextracted with dichloromethane
  4. washThe extracts were washed with saturated sodium chloride solution
  5. temperaturechilled
  6. filtrationFiltration

Sources & evidence

ORD record
ord-67693428054f43008f3e1f3d582b38bb
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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