Synthesis of resacetophenone

Preparation of resacetophenone

Alternative Names: 2′,4′-DIHYDROXYACETOPHENONE; 1-(2,4-Dihydroxyphenyl)ethanone; 89-84-9; 2,4-Dihydroxyacetophenone; 4-Acetylresorcinol; Resacetophenone;

Preparation of resacetophenone

Preparation of resacetophenone

30 g of fused zinc chloride are dissolved in 30 g of hot glacial acetic acid and 20 g of resorcinol added. Heating is continued in an open flask on a sand bath until (about 145-150° C) the liquid begins to boil vigorously, when the flame is removed, and the reaction left to complete itself on the hot sand bath. The temperature should not exceed 150° C, nor should it remain at 150° C for too long a time as resinous by-products are thus formed indicated by the reaction mixture becoming the deep red. After cooling, the product is thoroughly mixed with 200 ml of 2% aqueous hydrochloric acid to dissolve the zinc chloride, and the undissolved portion collected by filtration. This dark brown lustrous product is dissolved in sodium hydroxide solution, boiled with activated carbon and filtered. As resacetophenone is difficultly soluble in water it is precipitated from the filtrate by acidification with hydrochloric acid. It may, if necessary, be purified by a repetition of this treatment or by recrystallisation from 2% hydrochloric acid. Yield 40% theoretical (11 g). Needles, M.P. 142° C. Decomposes  on distillation even at reduced pressure.

Systematic organic chemistry, by W. M. Cumming, 91, 1937.

IUPAC Name

1-(2,4-dihydroxyphenyl)ethanone

InChI

InChI=1S/C8H8O3/c1-5(9)7-3-2-6(10)4-8(7)11/h2-4,10-11H,1H3

InChI Key

SULYEHHGGXARJS-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

2,4-dihydroxyacetophenone

Depositor-Supplied Synonyms

2′,4′-DIHYDROXYACETOPHENONE, 1-(2,4-Dihydroxyphenyl)ethanone, 89-84-9, 2,4-Dihydroxyacetophenone, 4-Acetylresorcinol, Resacetophenone, Resoacetophenone, 1-Acetyl-2,4-dihydroxybenzene, Resorcinol, 4-acetyl-, Ethanone, 1-(2,4-dihydroxyphenyl)-, Acetophenone, 2′,4′-dihydroxy-, .beta.-Resacetophenone, 1-(2,4-dihydroxy-phenyl)-ethanone, NSC 10883, 1-(2,4-dihydroxyphenyl)ethan-1-one, UNII-UC3V356VZC, 2,4-Dihydroxy Acetophenone, CHEMBL243374, CHEBI:18414, SULYEHHGGXARJS-UHFFFAOYSA-N, EINECS 201-945-3, BRN 1282505, AI3-00866, WLN: QR CQ DV1, 954-97-2, dihydroxyacetophenon, beta-Resacetophenone, PubChem3375, 2,4-dihyroxyacetophenone, AC1Q1JHT, 1-Acetylbenzene-2,4-diol, 4-Acetyl-1,3-benzenediol, AC1L1NR7, AC1Q5ED3, 2′,4′-Dihydroxyacetophenon, UC3V356VZC, SCHEMBL26357, KSC448A9T, BIDD:ER0659, D107409_ALDRICH, 2′,4′-Dihydroxy-acetophenone, ACMC-209r36, 1,3-Dihydroxy-4-acetylbenzene, 2”,4”-dihydroxyacetophenone, CTK3E8099, TIMTEC-BB SBB040836, ZINC38028, 2′,4′-DIHYDROXYACETOPHE, MolPort-000-482-777, 2,4-DIHYDROOXYACETOPHENONE, AKOS 90593, BB_SC-6691, KST-1B9444, NSC10883, NSC37559, STR03384, AKOS BBS-00004294, UKRORGSYN-BB BBR-007146, ANW-39376, AR-1B0165, BBL012128, BDBM50241221, NSC-10883, NSC-37559, SBB040836, STK084318, ZINC00038028, AKOS000119522, AC-1105, AS01140, FS-3456, MCULE-8687773185, RL05645, RTC-067541, TRA0025245, 4CN-0699, AJ-08777, AK-50224, AN-15263, BC676988, CJ-00226, KB-17586, LS-13469, OR025128, OR095364, SC-07232, ST053782, ZB001051, AB0000224, AB1002103, ST2414924, TC-067541, TL8005791, AM20041337, D0561, FT-0610122, C03663, S-1332, 4-08-00-01792 (Beilstein Handbook Reference), 3B4-0877, I01-2131, T7106635, W-100356, 1-Acetyl-2,4-dihydroxybenzene; 4-Acetylresorcinol; Resacetophenone, InChI=1/C8H8O3/c1-5(9)7-3-2-6(10)4-8(7)11/h2-4,10-11H,1H

Removed Synonyms

2-ACETYL RESORCINOL, Acetophenone,4′-dihydroxy-, Ethanone,4-dihydroxyphenyl)-, CID6990, ML 277, C412963, 105771-36-6, 1401242-74-7

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