10385-30-5

Basic information

• Product Name: 4-BENZYLOXYBUTYRIC ACID
• Synonyms: 4-BENZYLOXYBUTYRIC ACID;Butanoic acid,4-(phenylMethoxy)-;4-Benzyloxybutyric acid 95%
• CAS NO: 10385-30-5
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• EINECS: 1533716-785-6
• Product Categories: C11 to C12;Carbonyl Compounds;Carboxylic Acids
• Mol File: 10385-30-5.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 135 °C0.3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.097 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.66E-05mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.63±0.10(Predicted)
• CAS DataBase Reference: 4-BENZYLOXYBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXYBUTYRIC ACID(10385-30-5)
• EPA Substance Registry System: 4-BENZYLOXYBUTYRIC ACID(10385-30-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 10385-30-5(Hazardous Substances Data)

Usage

Uses

4-Benzyloxybutyric acid may be used in the synthesis of benzyloxybutyryl (BOB) esters of alcohols by standard acylation techniques or by the Jacobsen asymmetric nucleophilic ring opening of epoxides.

Synthesis Reference(s)

Tetrahedron, 53, p. 8853, 1997 DOI: 10.1016/S0040-4020(97)90396-3

General Description

4-Benzyloxybutyric acid can be synthesized from γ-butyrolactone. It participates in the asymmetric total synthesis of erythromycin.

InChI:InChI=1/C11H14O3/c12-11(13)7-4-8-14-9-10-5-2-1-3-6-10/h1-3,5-6H,4,7-9H2,(H,12,13)

Upstream product

• 41478-45-9 Diethyl<(2-benzyloxy)ethyl>malonate 
• 4541-14-4 4-benzyloxy-butan-1-ol 
• 96-48-0 4-butanolide 
• 100-44-7 benzyl chloride 
• 3153-37-5 methyl 4-chlorobutyrate 
• 20194-18-7 sodium phenyl-methanolate 
• 100-39-0 benzyl bromide 
• 502-85-2 sodium 4-hydroxybutanoate 
• 124-38-9 carbon dioxide 
• 54314-84-0 1-[(3-bromopropoxy)methyl]-benzene 
• 22273-77-4 ((but-3-yn-1-yloxy)methyl)benzene 
• 4541-15-5 5-(benzyloxy)-1-pentanol 
• 17229-17-3 benzyl 2-chloroethyl ether 
• 100-52-7 benzaldehyde 

Downstream Products

• 145122-41-4 5-(4'-Benzyloxy-1'-hydroxybutylidene)-2,2-dimethyl-1,3-dioxan-4,6-dione 
• 83005-55-4 2-(2-Benzyloxy-ethyl)-4-methyl-pent-4-enoic acid 
• 374590-18-8 (2S,5S)-N-(4-benzyloxybutyryl)-2,5-bis(methoxymethoxymethyl)pyrrolidine 
• 221615-79-8 4-Benzyloxy-butyric acid (1S,2S)-2-{4-[4-(4-{4-[(3R,5R)-5-(2,4-difluoro-phenyl)-5-[1,2,4]triazol-1-ylmethyl-tetrahydro-furan-3-ylmethoxy]-phenyl}-piperazin-1-yl)-phenyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1-methyl-butyl ester 
• 771431-34-6 C₁₃H₁₆O₄ 
• 1462260-13-4 (3S,8R)-8-(4-(benzyloxy)butanamido)heptadeca-1-en-4,6-diyn-3-yl acetate 
• 1458033-17-4 (R)-4-benzyl-3-((R)-4-(benzyloxy)-2-methylbutanoyl) oxazolidin-2-one 
• 96154-47-1 (R)-2-methyl-1,4-butanediol 4-benzyl ether 
• 1458033-18-5 (4S,5R)-7-(benzyloxy)-5-methylhept-1-en-4-ol 
• 1458033-19-6 C₁₇H₂₆O₃ 
• 1458033-20-9 (2R,3R,4R)-6-(benzyloxy)-3-(methoxymethoxy)-4-methylhexane-1,2-diol 
• 1458033-21-0 (R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane 
• 1458033-22-1 (5R,6R)-5-((R)-4-(benzyloxy)butan-2-yl)-13,13,14,14-tetramethyl-2,4,12-trioxa-13-silapentadec-8-yn-6-ol 
• 1618677-47-6 5-(3-benzyloxy-propyl)-3H-[1,3,4]oxadiazol-2-one 

Relevant articles and documents

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(Chemical Equation Presented) Catalytic use of o-iodoxybenzoic acid (IBX) in the presence of Oxone as a co-oxidant is demonstrated for the oxidation of primary and secondary alcohols in user- and eco-friendly solvent mixtures. Also demonstrated is the in situ (re)oxidation of 2-iodosobenzoic acid (IBA) and even commercially available 2-iodobenzoic acid (2IBAcid) by Oxone to IBX allowing one to use these less hazardous reagents, in place of potentially explosive IBX, as catalytic oxidants.

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A Novel Synthesis of Sex Pheromone from the Longicorn Beetle (Psacothea hilaris)

Abstract: An asymmetric synthesis of (8Z,21R)-21-methylpentatriacont-8-ene, the sex pheromoneof the yellow-spotted longicorn beetle Psacotheahilaris, has been achieved using Evan’s induction as the keystep. Based on the asymmetric methylation product of chiral (R)-4-benzyl-1,3-oxazolidin-2-one, the carbon chainof the target molecule was assembled through aC5+C12+C11+C8sequence. (2R)-4-(Benzyloxy)-2-methylbutan-1-ol, which can be obtained fromγ-lactone following Evan’s protocol, was connected to aC12 alkyl group. The chiral methyl group remained thekey moiety (97% ee). After another Wittigreaction and catalytic hydrogenation step, the designed key intermediate(13R)-13-methylheptacosan-1-ol wasobtained. Finally, after oxidation and Wittig reaction, the synthesis of thetarget molecule was completed in 10 linear steps with an ultra-high overallyield of 36.2%.

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The invention discloses a synthesis method of a sex pheromone (S)-14-methyl-1-octadecene of peach leaf miners, which comprises the following steps: carrying out ring opening on gamma-butyrolactone asa raw material, reacting the gamma-butyrolactone with benzyl chloride to generate 4-benzyloxybutyric acid, and reacting the 4-benzyloxybutyric acid with (S)-4-benzyl-2-oxazolidinone; performing reaction with methyl iodide under the action of organic base to induce chiral methyl; reducing the chiral methyl into alcohol under the action of lithium aluminum hydride, oxidizing the alcohol into aldehyde, and carrying out wittig reaction with triphenylpropylphosphonium bromide; after the Wittig reaction, using a Pt/C as a catalyst for catalytic hydrogenation to remove double bonds, removing benzyl with Pd/C as a catalyst to form alcohol, and oxidizing the alcohol into aldehyde; carrying out monobromination on 1, 10-decanediol, carrying out single protection by using TBSCl, and performing reaction with triphenylphosphine to obtain quaternary phosphonium salt; carrying out Wittig reaction on the aldehyde and the quaternary phosphonium salt, and using Pt/C as a catalyst for catalytic hydrogenation to eliminate double bonds; removing TBS single protection to form alcohol, and then oxidizing the alcohol into aldehyde; and reacting the aldehyde with methyltriphenylphosphonium bromide wittig toobtain the pheromone (S)-14-methyl-1-octadecene. According to the method, the reaction conditions are mild, chiral methyl is kept in the reaction process, and racemization is avoided.

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