Sulfuric Acid → HCID 14984871, compound

HRID 2051054Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[CH:5]=[C:4]([CH3:11])[CH:3]=1.C[O:13][C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[O-].[Na+].S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[C:14]([CH2:10][C:8](=[O:9])[C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[C:4]([CH3:11])[CH:5]=1)(=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 135 °C

Procedure

3,5-dimethylacetophenone (37.1 grams; 0.75 mol), methylbenzoate (156 grams; 1.0 mol) and xylene (308.6 grams) were placed into a four-necked round bottom one liter flask equipped as in Example 1. Sodium methoxide (16.4 grams; 0.30 mol) was added to the stirred reaction mixture under a blanket of nitrogen and the mixture was heated to 135° C. As the temperature of the mixture reached 100° C., solution began coming over. The temperature was held at about 135° C. for 6 hours after which time it was cooled to room temperature. Sulfuric acid (375 ml of 10% solution) was added slowly over a 30 minute period with stirring. The xylene layer was separated and washed with water, then with sodium carbonate solution (100 ml of 10% solution) and again with water (100 ml). Xylene was stripped off at 175° C. resulting in the desired product, benzoyl 3,5-dimethylbenzoylmethane (51 grams; 63 weight percent yield) having a melting point of 48°-53° C..

Workup

customequipped as in Example 1
customreached 100° C.
temperatureafter which time it was cooled to room temperature
customThe xylene layer was separated
washwashed with water
customwas stripped off at 175° C.

Sources & evidence

ORD record: ord-45e9c45a157c4711aabcf29a6066c21d
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05015777

Reaction notes

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