Methanol → 1,3-Propanedione, 1,3-bis(4-bromophenyl)-

HRID 10113

Reaction equation

HRID 10113 reaction equation
C[C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[H-].[Na+].[CH3:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)=[O:16].CO>C1C=CC=CC=1>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([C:15](=[O:16])[CH2:14][C:4](=[O:6])[C:3]2[CH:2]=[CH:10][C:9]([Br:11])=[CH:8][CH:7]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7466p-BromoacetophenoneHCID 24758Sodium hydrideHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 1474381,3-Propanedione, 1,3-bis(4-bromophenyl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
60 °C

Procedure

In a 1-liter three neck round bottom flask, 43 g (0.2 mol) methyl 4-bromobenzoic acid and 17.6 g (0.4 mol) sodium hydride were dissolved in 200 ml dried benzene and heated to 60° C. Next, 39.8 g (0.2 mol) 4-bromoacetophenone in 100 ml dry benzene was slowly added through a dropping funnel, and 1 ml methanol was added to the flask to initiate the reaction. After the mixture was refluxed overnight, the reaction was quenched by adding methanol and pouring it into ice water. The pH of the mixture was brought down to 7.0 using 5 N sulfuric acid. A solid was collected, washed with water, and recrystallized from benzene to give a light yellow product. Characterization. Yield: 30.3 g (40%). 1H NMR (300 MHz, CDCl3, 20° C., δ): 7.84 (d, 4H, ArH); 7.62 (d, 4H, ArH); 6.77 (s, 2H, CH2). EI-MS: 382 (M+), 301, 225, 183, 157.

Workup

  1. customthe reaction
  2. temperatureAfter the mixture was refluxed overnight
  3. customthe reaction was quenched
  4. additionby adding methanol
  5. additionpouring it into ice water
  6. customA solid was collected
  7. washwashed with water
  8. customrecrystallized from benzene
  9. customto give a light yellow product

Sources & evidence

ORD record
ord-439e7a687fe84598b3e1c881ce019501
Source dataset
uspto-grants-2006_08
Patent number
US07094121B2

Linked notes

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