2163-12-4

Basic information

• Product Name: 2,4-Diacetylresorcinol
• Synonyms: 2,4-Diacetyl-1,3-benzenediol;2,4-Diacetylresorcinol;2,6-Diacetylresorcinol;1,1'-(2,4-dihydroxy-1,3-phenylene)diethanone
• CAS NO: 2163-12-4
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• Mol File: 2163-12-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 88-89 °C
• Boiling Point: 170-172 °C(Press: 26 Torr)
• Appearance: /
• Density: 1.300±0.06 g/cm3(Predicted)
• PKA: 8.17±0.23(Predicted)
• CAS DataBase Reference: 2,4-Diacetylresorcinol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Diacetylresorcinol(2163-12-4)
• EPA Substance Registry System: 2,4-Diacetylresorcinol(2163-12-4)

Safety Data

• Hazardous Substances Data: 2163-12-4(Hazardous Substances Data)

Usage

Preparation

Obtained from resorcinol by a typical Friedel– Crafts reaction (40%) , ? with acetic acid in the presence of boron trifluoride, – at 140° for 3 h in a sealed tube (30%) ; – at 125° for 6 h (20%) ; ? with acetic anhydride, – in the presence of concentrated sulfuric acid at 130° for 15 min (15%) ; – in the presence of zinc chloride at 145–150° (7%) or at 150–160° for 20 min (6%) ; ? with acetyl chloride, – by heating in the presence of concentrated sulfuric acid (10%) ; – in ethyl ether in the presence of aluminium chloride at r.t. for 3 days (7%).

Upstream product

• 699-83-2 2,6-dihydroxylacetophenone 
• 64-19-7 acetic acid 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 7664-93-9 sulfuric acid 
• 108-24-7 acetic anhydride 
• 7446-70-0 aluminium trichloride 
• 42059-48-3 acetic acid 4-acetyl-3-hydroxyphenyl ester 
• 98-95-3 nitrobenzene 
• 108-58-7 Resorcinol diacetate 
• 108-46-3 recorcinol 
• 13031-39-5 3-chlorophenyl acetate 
• 108-43-0 3-monochlorophenol 
• 6883-54-1 5-acetyl-2,4-dihydroxy-benzoic acid methyl ester 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 

Downstream Products

• 107415-10-1 1,3-diacetyl-2,4-dimethoxy-benzene 
• 64857-81-4 2,6-Diacetyl-3-methoxy-phenol 
• 116470-08-7 6-Cinnamoyl-5-hydroxyflavanone 
• 116470-09-8 8-Cinnamoyl-7-hydroxyflavanone 
• 84422-44-6 3'-Acetyl-2',4'-dihydroxychalcone 
• 84422-45-7 8-Acetyl-7-hydroxyflavanone 
• 121824-30-4 2,4-di(3-methyl-3-hydroxybutyryl)resorcinol 
• 108981-98-2 6-acetyl-5-hydroxy-2-phenyl-chromen-4-one 
• 84422-46-8 3,3',5,5'-tetraacetyl-2,2',4,4'-tetrahydroxydiphenylmethane 
• 103264-32-0 3-acetyl-2,4-dihydroxy-5-nitroacetophenone 
• 2999-24-8 3,5-diacetyl-1,2,4-trihydroxybenzene 
• 54337-59-6 3'-ethyl-2',6'-dihydroxyacetophenone 
• 52959-33-8 2,4-diethyl-resorcinol 
• 2896-60-8 4-ethyl-1,3-benzenediol 

Relevant articles and documents

A re-investigation of the Fries rearrangement of 3-chlorophenyl acetate and synthesis of 2-azido-1-(4-(benzyloxy)-2-chlorophenyl)ethanone from 4-bromo-3-chlorophenol

The Fries rearrangement of 3-chlorophenyl acetate provided the expected 4-chloro-2-hydroxy-acetophenone as the major product and 2,4-diacetyl resorcinol and 2-chloro-4-hydroxy-acetophenone as minor products. 4-Benzyloxy-2-chloroacetophenone was prepared by a Heck reaction and then elaborated to 4-benzyloxy-2-chlorophenacyl azide.

Selective fries rearrangement catalyzed by zinc powder

Zinc powder in the presence of N,N-dimethylformamide efficiently catalyzes the selective Fries rearrangement of acetylated phenols under microwave heating or with conventional heating using an oil bath. In some cases different products were obtained using microwave heating and conventional heating. Selective migration of the acyl group has been noted with good yields.

Claisen Rearrangement of Prenyl Ethers of Isomeric Acetylnaphthols and Bisprenyl Ethers of 4,6- and 2,4-Diacetylresorcinols

Claisen rearrangements of the 3-methylbut-2-enyl(prenyl)ethers 3 and 9 of 2-acetyl-1-hydroxy- and 1-acetyl-2-hydroxynaphthalenes 1 and 2 and the bis(3-methylbut-2-enyl)ethers 12 and 18 of 2,4- and 4,6-diacetylresorcinols 11 and 17 have been studied under a variety of thermal and catalytic conditions. 2-Acetyl-4-(3-methylbut-2-enyl)naphthalene-1-ol 4 was the sole product on rearrangement of compound 3, in DMA or neat.Under catalytic conditions 3,4-dihydro-2,2-dimethyl-2H-naphthopyran 7 was obtained in poor yield.An isomeric pyran, 1,2-dihydro-3,3-dimethyl-3H-naphthopyran 10 (25-43percent) was obtained under both thermal and catalytic conditions from 9.The rearrangement of 12 under thermal conditions (DMA and neat) furnished 3-acetyl-2,4-dihydroxy-5-(3-methylbut-2-enyl)acetophenone 13 and 3,8-diisopropylbenzodifuran 14.Pd'' mediated rearrangement of 12 gave only the partially deprenylated ether, 3-acetyl-4-hydroxy-2-(3-methylbut-2-enyloxy)acetophenone 15 (29percent).While the isomeric ether 18 gave the monoprenyl ether, 5-acetyl-4-hydroxy-2-(3-methylbut-2-enyloxy)acetophenone 19 in quantitative yield (95percent).The rearrangment products were characterised and their formation rationalised in terms of allowed sigmatropic shifts( prenyl and H) followed by loss of prenyl or acetyl groups.The reactions of prenyl ethers are both comparable to those of the corresponding allyl ethers and consistent with the greater fixed double-bond character of the naphthalene system compared to that of benzene.Prenyl derivatives of benzene and naphthalene containing ortho - hydroxyacetophenone units were formed which have potential in synthesis.