14918-80-0

Basic information

• Product Name: 3-formylbut-2-enyl acetate
• Synonyms: 3-formylbut-2-enyl acetate;4-Acetyloxy-2-methyl-2-butenal;Acetic acid 3-formyl-2-butenyl ester;Einecs 238-989-8
• CAS NO: 14918-80-0
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.1525
• EINECS: 238-989-8
• Mol File: 14918-80-0.mol
• Article Data: 18

Chemical Properties

• Melting Point: 50-55 °C
• Boiling Point: 232.6 °C at 760 mmHg
• Flash Point: 96.5 °C
• Appearance: /
• Density: 1.027 g/cm³
• Vapor Pressure: 0.0586mmHg at 25°C
• Refractive Index: 1.438
• CAS DataBase Reference: 3-formylbut-2-enyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-formylbut-2-enyl acetate(14918-80-0)
• EPA Substance Registry System: 3-formylbut-2-enyl acetate(14918-80-0)

Safety Data

• Hazardous Substances Data: 14918-80-0(Hazardous Substances Data)

Usage

Synthesis

Vitamin A intermediated C5,namely 3- formylbut- 2- enyl acetate,which was used C15 + C5 synthesis route of vitamin A.?2- Chloro- 1- ethanol was used as starting material,esterified by acetic anhydride and protected by phosphate ester,and then reacted with 1,1- dimethoxy- 2propanone,trans- γ- acetoxytiglic aldehyde dimethyl acetal can be obtained,subsequently deprotection and 3- formylbut- 2- enyl acetate can be achieved.

Uses

3-Formylcrotyl Acetate can be used as a vitamin A intermediate.

InChI:InChI=1/C7H10O3/c1-6(5-8)3-4-10-7(2)9/h3,5H,4H2,1-2H3

Upstream product

• 38872-49-0 4-acetoxy-1-chloro-2-methyl-2-butene 
• 1515-76-0 1-acetoxybuta-1,3-diene 
• 201230-82-2 carbon monoxide 
• 55311-87-0 E,Z-4-bromo-3-methyl-1-acetoxy-2-butene 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 10523-96-3 3-methyl-3-butenyl chloride 
• 3330-25-4 4-chloro-2-methyl-2-buteneal 
• 127-08-2 potassium acetate 
• 127-09-3 sodium acetate 
• 74549-14-7 (E/Z)-4-Acetoxy-2-methyl-2-butenal-dimethylacetal 
• 1576-98-3 1,4-diacetoxybut-2-ene 
• 1438-14-8 2-isopropyloxirane 
• 14690-12-1 2-methyl-3-butenal 
• 29773-17-9 4-acetoxy-2-methylen-butanal 

Downstream Products

• 127-47-9 Retinol acetate 
• 27231-36-3 5-methyl-1H-benzoimidazole-2-thiol 
• 51575-59-8 C₁₀H₁₈O₃ 
• 4172-46-7 2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohex-1-enyl)heptadeca-2,4,6,8,10,12,14,16-octaenal 
• 1416548-67-8 4-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,7-dien-5-ynyl acetate 

Relevant articles and documents

Synthesis of analogues of citranaxanthin and their activity in free radical scavenging

Citranaxanthin and its analogues were synthesised via a C5 unit elongation to substituted conjugated polyenes. Their free radical scavenging activity was measured by 1,1-diphenyl-2-picrylhydrazinyl spectrophotometric methods. Results indicated that the new compounds exhibited antioxidant activities. Three new analogues had stronger antioxidant activity than citranaxanthin.

Process for preparation of 4-acetoxy-2-methyl-2-butene-1-aldehyde and intermediates thereof

The invention relates to the technical field of organic synthesis, and discloses a method for preparing 4-acetoxy-2-methyl-2-butene-1-aldehyde and an intermediate thereof. The method comprises the following steps: (1) in the presence of an esterification reagent, carrying out esterification reaction on 1, 4-butenediol to obtain 1, 4-butenediol diacetate; (2) in the optional presence of a first catalyst, carrying out an isomerization reaction on the 1, 4-butenediol diacetate to obtain 3, 4-diacetoxy-1-butene; (3) in the presence of a phosphorus-containing ligand and a rhodium catalyst and/or a cobalt catalyst, carrying out hydroformylation reaction on the 3, 4-diacetoxy-1-butene, carbon monoxide and hydrogen to obtain 2-methyl-3, 4-diacetoxy-1-butyraldehyde; (4) in the optional presence of a third catalyst, carrying out an elimination reaction on the 2-methyl-3, 4-diacetoxyl-1-butyraldehyde to obtain the 4-acetoxyl-2-methyl-2-butene-1-aldehyde. The method provided by the invention has the advantages of mild reaction conditions, environmental friendliness and high yield.

Preparation method of 4-acetoxy-2-methyl-2-butenal

The invention discloses a preparation method of 4-acetoxy-2-methyl-2-butenal, which takes salifying and wittig reactions as a core and methanol which is cheap and easy to obtain as a reaction initial raw material. The invention provides a new reaction route, the reaction steps are simple, the reaction conditions are mild, and the product yield is high.