Identification | Back Directory | [Name]
4-BENZYLOXYBUTYRIC ACID | [CAS]
10385-30-5 | [Synonyms]
CML-009 4-BENZYLOXYBUTYRIC ACID 4-Benzyloxybutyric acid 95% Butanoic acid,4-(phenylMethoxy)- | [EINECS(EC#)]
628-164-4 | [Molecular Formula]
C11H14O3 | [MDL Number]
MFCD01321257 | [MOL File]
10385-30-5.mol | [Molecular Weight]
194.23 |
Chemical Properties | Back Directory | [Boiling point ]
135 °C/0.3 mmHg (lit.) | [density ]
1.097 g/mL at 25 °C (lit.) | [refractive index ]
n20/D 1.512(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Oil | [pka]
4.63±0.10(Predicted) | [color ]
Colourless to Pale Yellow | [InChI]
InChI=1S/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) | [InChIKey]
CXEFZVVLTJQWBF-UHFFFAOYSA-N | [SMILES]
C(O)(=O)CCCOCC1=CC=CC=C1 |
Hazard Information | Back Directory | [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. | [Synthesis]
(1) Synthesis of 4-benzyloxybutyric acid: 4.0 g (60%, 0.1 mol) of sodium hydride was washed in hexane and mixed with 30 mL of anhydrous DMSO, the resulting mixture was stirred at 60°C in an oil bath for 1 hour. The mixture was cooled to room temperature under nitrogen protection and 100 mL of dry DMSO solution containing 12.6 g (0.1 mol) of sodium 4-hydroxybutyrate was added. After stirring for 2 hours at room temperature, the reaction solution was cooled in an ice bath, 0.2 mol of benzyl bromide was added slowly and the reaction continued for 2 hours at room temperature. After completion of the reaction, 0.5 L of ether was added, the mixture was filtered, the residue was washed with ether (300 mL x 3) and the filtrate was concentrated in vacuum. The concentrated residue was mixed with 100 mL of methanol, 100 mL of 8% sodium hydroxide solution was added, and the mixture was stirred at 60°C for 15 hours. After vacuum drying, the concentrated residue was washed with ether (200 mL x 2) and the ether layer was extracted with 1N sodium hydroxide (50 mL). All aqueous layers were combined and the pH was adjusted to <4 with concentrated hydrochloric acid and then extracted with ether (100 mL x 5). The ether layer was then extracted with 2N sodium hydroxide (50 mL x 3) and all aqueous layers were again neutralized with concentrated hydrochloric acid to pH <4 and extracted with ether. The resulting product was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuum to give 9.42 g of 4-benzyloxybutyric acid as a light yellow oil in 49.5% yield.NMR (500 MHz, CDCl3): δ 1.95 (2H, dt, J = 6 and 7 Hz, β-CH2), 2.50 (2H, t, J = 7 Hz, α-CH2), 3.54 (2H, t, J = 6 Hz, γ-CH2), 4.52 (2H, s, PhCH2O), 7.25-7.4 (5H, m, C6H5), 10.0-10.8 (1H, br, CO2H); IR (pure): ν 1710 cm-1 (COOH); FAB-MS: m/z = 195 (M + H+). | [References]
[1] Patent: US6057431, 2000, A |
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Energy Chemical
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