| Identification | Back Directory | [Name]
(2-HYDROXY-PHENYL)-ACETIC ACID METHYL ESTER | [CAS]
22446-37-3 | [Synonyms]
Einecs 245-004-5
Methyl o-hydroxyphenylacetate
Methyl 2-hydroxybenzeneacetate
METHYL 2-HYDROXYPHENYL ACETATE
Methyl 2-(2-hydroxyphenyl)acetate
2-Hydroxybenzeneacetic acid methyl ester
(2-HYDROXY-PHENYL)-ACETIC ACID METHYL ESTER
Benzeneacetic acid, 2-hydroxy-, methyl ester
Acetic acid, (o-hydroxyphenyl)-, methyl ester | [EINECS(EC#)]
245-004-5 | [Molecular Formula]
C9H10O3 | [MDL Number]
MFCD00090077 | [MOL File]
22446-37-3.mol | [Molecular Weight]
166.17 |
| Chemical Properties | Back Directory | [Melting point ]
122-124℃ | [Boiling point ]
115-120℃ (0.3 Torr) | [density ]
1.181±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform, Methanol (Slightly) | [form ]
Solid | [pka]
9.55±0.30(Predicted) | [color ]
Off-White to Light Brown | [InChI]
InChI=1S/C9H10O3/c1-12-9(11)6-7-4-2-3-5-8(7)10/h2-5,10H,6H2,1H3 | [InChIKey]
BVBSGGBDFJUSIH-UHFFFAOYSA-N | [SMILES]
C1(CC(OC)=O)=CC=CC=C1O |
| Hazard Information | Back Directory | [Uses]
Methyl 2-(2-Hydroxyphenyl)acetate is used as a reactant in the preparation of caffeic acid phenylethyl esters as ?antiproliferative agents. | [Definition]
ChEBI: Methyl (2-hydroxyphenyl)acetate is a member of phenols. | [Synthesis Reference(s)]
Synthetic Communications, 24, p. 2743, 1994 DOI: 10.1080/00397919408010590 | [Synthesis]
Preparative Example 1A: Synthesis of methyl 2-hydroxyphenylacetate: o-hydroxyphenylacetic acid (400 g, 2.63 mmol) was dissolved in methanol (3.0 L), and the esterification reaction was carried out by passing hydrogen chloride gas into the solution. The reaction was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the reaction mixture was concentrated and dried under vacuum to afford the title compound 1A (415 g, 95% yield), the product was initially a yellow oil and solidified to a solid after standing overnight. The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 7.20-7.16 (m, 1H), 7.11-7.09 (m, 1H), 6.93-6.86 (m, 2H), 4.48 (br s, 1H), 3.74 (s, 2H), 3.69 (s, 3H). | [References]
[1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 31, p. 5147 - 5155
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8948 - 8952
[3] Organic Letters, 2008, vol. 10, # 18, p. 3969 - 3972
[4] Patent: WO2015/102990, 2015, A1. Location in patent: Paragraph 0193-0195
[5] Journal of Organic Chemistry, 1994, vol. 59, # 1, p. 203 - 213 |
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