Acetic Acid → Dibenzoylmethane

HRID 2188354Notes

Reaction equation

HRID 2188354 reaction equation
[OH2:1].[C:2]1([CH:8]([CH3:10])C)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC.[Na].[C:15]([OH:18])(=O)[CH3:16]>>[C:15]([CH2:10][C:8](=[O:1])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:18])[C:16]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 5

HCID 176Acetic Acid2×HCID 962WaterHCID 1068Dimethyl SulfideHCID 7406CumeneHCID 5360545Sodium

Product 1

HCID 8433Dibenzoylmethane

Procedure

Into a two liter beaker equipped with a mechanical stirrer, 500 mL of water and 250 mL of cumene were added. A ph-stat (Metrohm titrator, model 716 DMS, Brinkmann Instruments) was set up to add acetic acid to pH 7. The sodium salt of DBM was added slowly to the beaker. The pH varied between 5 and 7.5; 14.7 mL of acetic acid was added. The two layers were transferred to a separation funnel, the aqueous layer was removed, and the organic layer was washed with aqueous sodium bicarbonate and then with water. The organic layer was then concentrated under vacuum in a rotary evaporator. The residue was crystallized from 90% isopropanol, affording DBM (53.58 g, 96% yield) having a purity of more than 99% (GC).

Workup

  1. customInto a two liter beaker equipped with a mechanical stirrer
  2. customThe two layers were transferred to a separation funnel
  3. customthe aqueous layer was removed
  4. washthe organic layer was washed with aqueous sodium bicarbonate
  5. concentrationThe organic layer was then concentrated under vacuum in a rotary evaporator
  6. customThe residue was crystallized from 90% isopropanol
  7. customaffording DBM (53.58 g, 96% yield)

Sources & evidence

ORD record
ord-bb821ca3f92e4e38b99d8401ce070603
Source dataset
uspto-grants-2002_06
Patent number
US06410795B1

Reaction notes

Loading…