An efficient synthesis of diacetates from aldehydes using beta zeolite

An effective method for the selective synthesis of geminal diacetates (acylals) from aromatic aldehydes using alumina-supported InCl3

“…The acylals are important starting materials for the synthesis of valuable intermediates in the Diels-Alder cycloaddition reactions [3]. Acylals have been applied as crosslinking reagents for cellulose in cotton [4].…”

Silica Sulfuric Acid as an Efficient Heterogeneous Catalyst for the Synthesis of 1,1-Diacetates under Solvent-Free Conditions

“…By using this catalyst, various aldehydes were converted to their corresponding diacetates in good yields and short reaction times (Table 2). Aliphatics and a,b-unsaturated aldehydes produced acylals in good yields ( Table 2, entries, [17][18][19][20]. Furfural is converted to its 1,1-diacetate in moderate yield ( Table 2, entry 16), 4-(N,N-dimethylamino)benzaldehyde failed to give 1,1-diacetate under the same conditions which may be due to electron donation of the dimethylamino group (Table 2, entry 21).…”

“…3,4 Moreover, the acylal functionality can be converted into other functional groups by reaction with appropriate nucleophiles. 5, 6 Some of the reported reagents for the preparation of 1,1-diacetates from aldehydes and acetic anhydride include sulfuric acid, 7 triflic acid, 8 PCl 3 , 9 I 2 , 10 FeCl 3, 2,11 NBS, 12 Sc(OTf) 3 , 13 Cu(OTf) 2 , 14 Bi(OTf) 3 , 15 CAN, 16 AlPW 12 O 40 , 17 b-Zeolite, 18 LiBF 4 , 19 Zn-Montmorillonite, 20 In(OTf) 3 , 21 H 2 NSO 3 H, 22 ZrCl 4 , 23 Bi(NO 3 ) 3 ·5H 2 O, 24 and Wells-Dawson acid (H 6 P 2 W 18 O 62 ·24H 2 O). 25 Although some of these methods have convenient protocols with good to high yields, the majority of these methods suffer at least from one of the following disadvantages: reaction under oxidizing conditions, high temperature, long reaction times, moisture sensitivity of the used reagent, high cost and high toxicity.…”

Preparation and characterization of chloroacetylated polystyrene‐supported zinc complexes and evaluation of their catalytic activities for the synthesis of 1,1‐diacetates

“…Moreover, the acylal functionality can be converted into other functional groups by reaction with appropriate nucleophiles 17, 18. Some of the reported reagents for the preparation of 1,1‐diacetates from aldehydes and acetic anhydride include sulfuric acid,19 triflic acid,20 PCl 3 ,21 FeCl 3 ,16 n‐bromosuccinimide (NBS),22 β‐zeolite,23 LiBF 4 ,24 H 2 NSO 3 H,25 H 3 PW 12 O 40 /MCM‐41,26 [Hmim] HSO,27 P 2 O 5 /Al 2 O 3 ,28 and Bi(NO 3 ) 2 ·5H 2 O 29. Although some of these methods have convenient protocols with good to high yields, the majority of these methods suffer from at least one of the following disadvantages: reaction under oxidizing conditions, high temperature, or long reaction times; moisture sensitivity of the used reagent; high cost and high toxicity; tedious workup; and environmental pollution.…”