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

HRID 355616

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

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 f umnel, 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 5N 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

additionwas added to the flask
customthe reaction
temperatureAfter the mixture was refluxed overnight
customthe reaction was quenched
additionby adding methanol
additionpouring it into ice water
customA solid was collected
washwashed with water
customrecrystallized from benzene
customto give a light yellow product

Sources & evidence

ORD record: ord-caee3de8e69648dcbc763c5f24300194
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834100

Linked notes

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