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Dimethylformamide → 1-(4-Methyl-4-{4-[(propan-2-yl)oxy]phenyl}pentyl)-3-phenoxybenzene

HRID 543273
Notes
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Reaction equation

HRID 543273 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)([CH3:19])[CH3:18])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:33](Br)([CH3:35])[CH3:34].CN(C)C=O>O>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH:33]([CH3:35])[CH3:34])=[CH:24][CH:25]=2)([CH3:19])[CH3:18])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 10980903Phenol, 4-[1,1-dimethyl-4-(3-phenoxyphenyl)butyl]-

Product 1

HCID 135564721-(4-Methyl-4-{4-[(propan-2-yl)oxy]phenyl}pentyl)-3-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.5 g of 1-(3-phenoxyphenyl)-4-(4-hydroxyphenyl)-4-methylpentane, 1.5 g of K2CO3, 3 ml of isopropyl bromide and 20 ml of dimethylformamide was stirred at 130° C. for two hours. The reaction mixture was poured into water and extracted with benzene. The benzene extract was washed with water and dried, and the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: benzene) to give 0.3 g of 1-(3-phenoxyphenyl)-4-(4-isopropoxyphenyl)-4-methylpentane.

Workup

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. washwas washed with water
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: benzene)

Sources & evidence

ORD record
ord-fa36a220706343ccb04c27a94a5020ff
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04661501

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes