Synthesis of acetophenone

Preparation of acetophenone

Preparation of acetophenone from benzene and acetyl chloride

Preparation of acetophenone

Preparation of acetophenone

The the round bottom flask fitted with reflux condenser and dropping funnels 200 g of anhydrous aluminium chloride are covered with 160 g parts of dry carbon disulfide. To the reaction flask from the dropping funnels which are connected to a pipe reaching below the level of the liquid 130 g of acetyl chloride and 150 g of dry thiophene-free benzene are added slowly. A vigorous reaction takes place, and is kept under control by regulating the rate of addition of the acetyl chloride and benzene. When all reactants have been added and the evolution of gaseous hydrogen chloride has slowed down, the mixture is refluxed for 30 minutes. The reaction is cooled to room temperature and poured in ice-water. The lower layer consists of acetophenone dissolved in carbon disulfide. This layer is separated, washed with alkaline solution in order to remove hydrochloric acid, dried, the solvent removed and the acetophenone purified by distillation in vacuo. Acetophenone forms colorless crystals with melting point 20° C, boiling point 201° C. Acetophenone is insoluble in water, but soluble in alcohol and many organic solvents.

Organic medical chemicals, by M. Barrowliff, 16-17, 1921

Preparation of acetophenone from calcium benzoate and calcium acetate

Preparation of acetophenone from calcium benzoate and calcium acetate

Preparation of acetophenone from calcium benzoate and calcium acetate

Fine powdered 100 g of anhydrous calcium benzoate and 50 g of dry calcium acetate are mixed and this mixture is introduced into an iron tube closed at one end and attached by a long air condenser to a receiver. The tube is heated strongly in a combustion furnace, beginning at the open end. A brown oil distills. The distillate is dehydrated over calcium chloride, decanted, and fractionated. A small quantity of a colorless liquid first distill, when the temperature rises quickly to 195° C, and the product, boiling at 195-205° C, is separately collected. This is redistilled and collected at 198-202° C. Acetophenone crystallizes on cooling.

A Class-Book of Organic Chemistry, by J. B. Cohen, 8, 1919

IUPAC Name

1-phenylethanone

InChI

InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3

InChI Key

KWOLFJPFCHCOCG-UHFFFAOYSA-N

Canonical SMILES

CC(=O)C1=CC=CC=C1

MeSH Synonyms

acetophenone

Depositor-Supplied Synonyms

ACETOPHENONE, 1-Phenylethanone, Methyl phenyl ketone, Acetylbenzene, 98-86-2, Ethanone, 1-phenyl-, Phenyl methyl ketone, Acetophenon, Benzoyl methide, Hypnone, Acetylbenzol, 1-Phenyl-1-ethanone, Benzene, acetyl-, Benzoylmethide, Phenylethanone, USAF EK-496, 1-phenyl-ethanone, RCRA waste number U004, Acetofenon [Czech], Ketone, methyl phenyl, Acetofenon, methylphenylketone, RCRA waste no. U004, NSC 7635, 1-phenylethan-1-one, Ketone, methyl phenyl-, FEMA Number 2009, UNII-RK493WHV10, AI3-00575, FEMA No. 2009, CCRIS 1341, CHEMBL274467, HSDB 969, CHEBI:27632, 4-acetyl-benzene, KWOLFJPFCHCOCG-UHFFFAOYSA-N, EINECS 202-708-7, SBB040241, DSSTox_CID_1828, DSSTox_RID_76353, DSSTox_GSID_21828, CAS-98-86-2, AC0, Dymex, phenylmethylketone, Ethanone,1-phenyl, methyl-phenyl ketone, AC1Q1JXH, SCHEMBL737, ACMC-209sb9, bmse000286, AC1L1OP7, WLN: 1VR, C8H8O, A10701_ALDRICH, KSC448E4P, ARONIS25343, W200905_ALDRICH, 442438_SUPELCO, RK493WHV10, SCHEMBL8170205, SCHEMBL13341485, 00790_FLUKA, 42163_FLUKA, A10701_SIAL, NSC7635, MolPort-000-871-218, NSC-7635, Tox21_202422, Tox21_300343, ANW-40963, c0117, ZINC00896628, AKOS000119011, DB04619, LS-2538, MCULE-4710225344, RP19373, RTR-025760, NCGC00248000-01, NCGC00248000-02, NCGC00254370-01, NCGC00259971-01, AJ-24240, AK110129, AN-24497, BC206207, K773, SC-18041, ZB015099, KB-160359, ST2406627, 4CH-018671, 624-EP2270006A1, 624-EP2272835A1, 624-EP2272844A1, 624-EP2275411A2, 624-EP2275418A1, 624-EP2275427A1, 624-EP2284165A1, 624-EP2301923A1, 624-EP2301983A1, 624-EP2305672A1, 624-EP2305682A1, 624-EP2308848A1, 624-EP2308851A1, 624-EP2308857A1, 624-EP2308865A1, 624-EP2308869A1, 624-EP2308879A1, 624-EP2311846A1, 624-EP2314295A1, 624-EP2314558A1, 624-EP2314583A1, 624-EP2371831A1, A0061, FT-0631709, FT-0694812, ST45054137, C07113, 36678-EP2308851A1, 36678-EP2311801A1, 36678-EP2311802A1, 36678-EP2311803A1, 36678-EP2371814A1, 37407-EP2311802A1, 37407-EP2311803A1, 3B4-2715, I01-6127, T7106872, 3B3-024347, 3B3-024348, InChI=1/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H

Removed Synonyms

Hypnon, CID7410, C038699, 103-84-4, 17537-31-4, ACE

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