Preparation of benzoylacetone
Alternative Names: Benzoylacetone; 1-Phenylbutane-1,3-dione; 1-PHENYL-1,3-BUTANEDIONE; 93-91-4; 1-Benzoylacetone; 1,3-Butanedione, 1-phenyl-;
Preparation of benzoylacetone
6 g of fresh prepared dry sodium ethoxide are added to 20 g of dry ethyl acetate under cooling by water. After 15 minutes, 10 g of acetophenone are added; the separation of the sodium salt of benzoylacetone immediately begins. A little dry ether is added, and in 4 hours the sodium compound is filtered off, washed with ether, air-dried, dissolved in cold water, and the solution acidified with acetic acid. Benzoyl acetone separates. Yield 66% theoretical (10 g). Colourless crystals; insoluble in water; m.p. 61° C;
Systematic organic chemistry, by W. M. Cumming, 97, 1937.
Preparation of benzoylacetone using sodium amide
25 g of ethyl acetate and 30 g of acetophenone are dissolved in 200 ml of anhydrous ether. To this is slowly added with gentle cooling 20 g of powdered sodium amide. It is then set aside for 24 hours, when the sodium salt separates, and is poured on to a mixture of ice and water sufficient to dissolve it completely. The aqueous layer is separated, and the ether removed from it by passing air through. Acetic acid is then added until the solution is acid, the precipitated benzoylacetone being filtered off and washed with water. Yield 75% theoretical (30 g). Colourless crystals; m.p. 61° C; insoluble in water.
Systematic organic chemistry, by W. M. Cumming, 98, 1937.
IUPAC Name
InChI
InChI=1S/C10H10O2/c1-8(11)7-10(12)9-5-3-2-4-6-9/h2-6H,7H2,1H3
InChI Key
CVBUKMMMRLOKQR-UHFFFAOYSA-N
Canonical SMILES
CC(=O)CC(=O)C1=CC=CC=C1
MeSH Synonyms
1-phenyl-1,3-butanedione, benzoylacetone
Depositor-Supplied Synonyms
Benzoylacetone, 1-Phenylbutane-1,3-dione, 1-PHENYL-1,3-BUTANEDIONE, 93-91-4, 1-Benzoylacetone, 1,3-Butanedione, 1-phenyl-, Acetoacetophenone, Acetylbenzoylmethane, 2-Acetylacetophenone, 1-Benzoyl-2-propanone, 2-Propanone, benzoyl-, Benzoyl-aceton, .alpha.-Acetylacetophenone, alpha-Acetylacetophenone, Benzoyl-aceton [German], NSC 4015, 1-Phenyl-1,3-butanedion, CVBUKMMMRLOKQR-UHFFFAOYSA-N, EINECS 202-286-4, BRN 0742413, AI3-10572, benzoyl acetone, acetyl acetophenone, DSSTox_CID_1803, 1-phenyl-1,3-butandione, ACMC-209ro2, AC1L1O5P, AC1Q1K1U, DSSTox_RID_76337, omega-ACETYLACETOPHENONE, UNII-I3RUV8U115, 1-phenyl-butane-1,3 dione, 1-phenyl-butane-1,3-dione, DSSTox_GSID_21803, SCHEMBL15116, B11907_ALDRICH, 1-BENZOYLACETONE,98%, AC1Q5F12, I3RUV8U115, CHEMBL3186793, 12830_FLUKA, NSC4015, MolPort-000-667-917, BB_SC-0115, ACT07622, NSC-4015, STR01075, Tox21_202879, ANW-40128, AR-1C5172, BBL011014, NSC100655, SBB040798, STK802149, AKOS000119529, ZINC100006468, MCULE-5543155182, NE10611, NSC-100655, PS-3611, RTR-030564, TRA0002644, CAS-93-91-4, NCGC00260425-01, AK161752, AN-42671, KB-64903, LS-45895, OR011201, OR089766, OR378483, SC-23803, ST092313, AB1003648, DB-010994, TR-030564, FT-0622746, ST24038177, X6797, B-0690, 4-07-00-02151 (Beilstein Handbook Reference), I01-6186, 3B3-034177, InChI=1/C10H10O2/c1-8(11)7-10(12)9-5-3-2-4-6-9/h2-6H,7H2,1H
Removed Synonyms
1, 1-phenyl-, CID7166, CID5387100, P0160, 1,3-BUTANEDIONE,1-PHENYL BENZOYLACETONE, C035851, 2-BENZYL 4-(TERT-BUTYL) 3-(3-METHOXY-3-OXOPROPYL)-5-METHYL-1H-PYRROLE-2,4-DICARBOXYLATE, 53365-80-3, 99585-88-3
