869-29-4

Basic information

• Product Name: ALLYLIDENE DIACETATE
• Synonyms: ALLYLIDENE DIACETATE;ACROLEIN DIACETATE;1,1-DIACETOXY-2-PROPENE;2-PROPENYLIDENE DIACETATE;2-PROPENE-1,1-DIOL DIACETATE;3,3-DIACETOXY-1-PROPENE;,3-Diacetoxy-1-propene;1-(Acetyloxy)-2-propenyl acetate
• CAS NO: 869-29-4
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• EINECS: 212-789-0
• Product Categories: monomer
• Mol File: 869-29-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: -37.6°C
• Boiling Point: 180°C (estimate)
• Flash Point: 78.3 °C
• Appearance: /
• Density: 1.0760
• Vapor Pressure: 0.915mmHg at 25°C
• Refractive Index: 1.4193 (estimate)
• CAS DataBase Reference: ALLYLIDENE DIACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYLIDENE DIACETATE(869-29-4)
• EPA Substance Registry System: ALLYLIDENE DIACETATE(869-29-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 869-29-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 1765, 1983 DOI: 10.1021/jo00158a036

Purification Methods

Check the NMR spectrum. If it is not satisfactory, then add Ac2O and a drop of conc H2SO4 and heat at 50o for 10minutes. Then add anhydrous NaOAc (ca 3g/ 100g of liquid) and fractionate. Note that it forms an azeotrope with H2O, so do not add H2O at any time. It is a highly flammable and TOXIC liquid; keep away from the skin. [Smith et al. J Am Chem Soc 73 5282 1951, Beilstein 2 H 154, 2 I 72, 2 III 356, 2 IV 291.]

InChI:InChI=1/C7H10O4/c1-4-7(10-5(2)8)11-6(3)9/h4,7H,1H2,2-3H3

Upstream product

• 187737-37-7 propene 
• 64-19-7 acetic acid 
• 74-98-6 propane 
• 124-38-9 carbon dioxide 
• 108-24-7 acetic anhydride 
• 107-02-8 acrolein 
• 500349-34-8 1,1,3-triacetoxy-propane 
• 91-22-5 quinoline 
• 2973-10-6 diisopropyl sulfate 

Downstream Products

• 61062-74-6 Acetic acid 1-acetoxy-3-chloro-2-(4-chloro-phenylsulfanyl)-propyl ester 
• 63888-20-0 3-phenyl-1-propen-1-yl acetate 
• 122570-98-3 Acetic acid (E)-4-(benzhydrylidene-amino)-4-(diethoxy-phosphoryl)-but-1-enyl ester 
• 122570-99-4 Acetic acid 1-[(benzhydrylidene-amino)-(diethoxy-phosphoryl)-methyl]-allyl ester 
• 35468-97-4 1-heptenyl acetate 
• 109-60-4 1-Propyl acetate 
• 591-87-7 Allyl acetate 
• 50-78-2 aspirin 
• 77104-99-5 C₁₅H₂₀O₂ 
• 914912-36-0 C₁₅H₂₀O₂ 
• 64847-78-5 (E)-1,1-diacetoxy-3-phenylprop-2-ene 
• 37973-55-0 Acetic acid (E)-1-acetoxy-3-(4-methoxy-phenyl)-allyl ester 
• 2206-62-4 1-(Diacetoxy-methyl)-2-acetoxy-3.5-diaethyl-1.2.5.6-tetrahydro-benzol 

Relevant articles and documents

Synthesis method of tert-butyl phenylpropionaldehyde

The invention discloses a synthesis method of tert-butyl phenylpropionaldehyde and relates to the field of perfume raw material synthesis, the method comprises the following steps: 1) synthesis of allylidene di(acetate)(AEDA): acetic anhydride and acrolein react at a certain temperature under the action of a catalyst A to obtain AEDA, 2) synthesis of a bourgeonal(BGA) precursor: tert-butylbenzeneand AEDA react at a certain temperature under the action of a catalyst B to obtain ortho-position and para-position BGA precursors, and 3) alcoholysis on the BGA precursor to prepare the BGA: the BGAprecursor, a solvent and a catalyst C react at a certain temperature to obtain the ortho-BGA and the para-BGA. Tert-butylbenzene is used as an initial raw material, acrolein is subjected to aldehyde group protection by acetic anhydride, then condensation is performed to obtain precursors of ortho-position and para-position bordeaux aldehyde, and an ortho-position and para-position tert-butylphenylpropionaldehyde mixed product is obtained through aldehyde group protection removal by hydrolysis, and the method is simple in process, low in raw material price, less in three wastes and elegant in fragrance, and can realize mass production.

Gallium-Catalyzed Scriabine Reaction

γ-Aryl enol acetates are easily obtained from diacetoxy alkenes and electron-rich arenes at room temperature using GaCl3 as catalyst. The products can then be converted into β-aryl aldehydes. This method represents the first broadly applicable catalytic version of the Scriabine reaction. DFT computations shed light on the mechanism of this transformation.

Process for producing allyl alcohol

A process for producing allyl alcohol is disclosed. The process comprises reacting propylene, acetic acid, and oxygen to produce a reaction mixture. The reaction mixture is distilled to produce a vapor stream comprising propylene and a liquid stream comprising allyl acetate, acetic acid, acrolein, and allyl diacetate. The liquid stream is distilled to produce a lights stream comprising acrolein; a side draw comprising allyl acetate, acetic acid, and water; and a bottoms stream comprising acetic acid and allyl diacetate. The bottoms stream is distilled to remove a heavies stream comprising allyl diacetate. The side draw is hydrolyzed to produce allyl alcohol.