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P-Cresol → 1-(4-Tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene

HRID 1450525
Notes
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Reaction equation

HRID 1450525 reaction equation
Br[CH:2]([C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[CH:3](Br)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1.[CH3:23][C:24]1[CH:30]=[CH:29][C:27]([O-:28])=[CH:26][CH:25]=1.[Na+].CC1C=CC(O)=CC=1>C1COCC1>[C:24]1([CH3:23])[CH:30]=[CH:29][C:27]([O:28][C:2]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)=[CH:3][C:4](=[O:12])[C:5]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=2)=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2879P-CresolHCID 117313561,2-Dibromo-1,2-di(4-bromobenzoyl)ethaneHCID 23673456Sodium p-methylphenolate

Product 1

HCID 539578091-(4-Tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,2-dibromo-1,2-di(4-bromobenzoyl)ethane (11.1 g, 0.02 mole) in 35 ml of THF was added a suspension of sodium 4-methyl phenoxide [prepared from 0.92 g (0.04 mole) Na and 4.32 g (0.04 mole) 4-methylphenol in 30 ml THF by refluxing for 4-5 hr]. The yellow mixture was refluxed for 2-3 hr (TLC followed) after which the THF was removed under reduced pressure. The residue was treated with water, and the solid was filtered, washed with water, dried (Na2SO4), and dissolved in chloroform. The chloroform solution was passed through a silica column (elution with 2-5% ether in hexane). The result was an off white crystalline solid, 4.95 g (50%), mp 137°-8° C. IR (KBr) 3087, 3035, 2868, 1687, 1646, 1587, 1572, 1557, 1502, 1399, 1364, 1194, 1068, 1009, 971, 876, 815, 772, 526. 1H NMR (CDCl3 /35° C.) 7.92 (d, 2H, J=8.8), 7.65 (d, 2H, J=8.8), 7.55 (d, 2H, J=8.8), 7.48 (d, 2H, J=8.8), 7.27 (d, 2H, J=8.3), 7.11 (d, 2H, J=8.3), 6.32 (s, 1H), 2.4 (s, 3H). 13C NMR (CDCl3 /35° C.) 189.4, 187.6, 168.4, 150.9, 136.6, 136.0, 133.4, 132.3, 131.8, 130.9, 130.3, 129.6, 129.2, 128.2, 120.6, 101.8, 20.95. MS m/e 500 (M+).

Workup

  1. customwas removed under reduced pressure
  2. additionThe residue was treated with water
  3. filtrationthe solid was filtered
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. dissolutiondissolved in chloroform
  7. washThe chloroform solution was passed through a silica column (elution with 2-5% ether in hexane)

Sources & evidence

ORD record
ord-1c9acdbcddb64b6cbef00c6334918960
Source dataset
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05602172

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes