62296-03-1

Basic information

• Product Name: 1,3-Propanediol, 1-phenyl-, 3-acetate
• CAS NO: 62296-03-1
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Mol File: 62296-03-1.mol

Chemical Properties

• CAS DataBase Reference: 1,3-Propanediol, 1-phenyl-, 3-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Propanediol, 1-phenyl-, 3-acetate(62296-03-1)
• EPA Substance Registry System: 1,3-Propanediol, 1-phenyl-, 3-acetate(62296-03-1)

Safety Data

• Hazardous Substances Data: 62296-03-1(Hazardous Substances Data)

Upstream product

• 4850-49-1 1-phenyl-1,3-propanediol 
• 108-24-7 acetic anhydride 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 127-08-2 potassium acetate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 581-55-5 benzylidene 1,1-diacetate 
• 873-49-4 cyclopropylbenzene 
• 563-63-3 silver(I) acetate 

Downstream Products

• 7334-41-0 3-acetoxypropiophenone 
• 22216-21-3 1-Phenyl-3-acetoxy-propylpentoxymethyl-aether 
• 22216-22-4 1-Phenyl-3-acetoxy-diaethylaminomethyl-aether 
• 154727-16-9 (R)-1-phenylpropane-1,3-diyl diacetate 
• 100-52-7 benzaldehyde 
• 91352-64-6 1-Phenyl-propandiol-(1,3)-1-methoxy-methylether 
• 5650-41-9 3-hydroxy-1-phenylpropan-1-one 
• 2538-52-5 1,3-diphenyl-4,5-dihydro-1H-pyrazole 

Relevant articles and documents

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols

Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.

Cobalt(II) Chloride Catalyzed Acylation of Alcohols with Acetic Anhydride: Scope and Mechanism

Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield.Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones.Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate.The β-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting β-acetoxy carbonyl compound is observed.A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene.A mechanism for these acylations is proposed by invoking an electron-transfer process.