No renderable structure data available
CCOC(=O)C(CC1=CC=CC=C1)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | ethyl 2-hydroxy-3-phenylpropanoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 15399-05-0 |
| Database ID | 6429708 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
ethyl 2-hydroxy-3-phenylpropanoate (CAS 15399-05-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 6429708
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f52e6d29d3fb4a2fbdc7a4f772c95129Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7ea74ea3223e4267bf22469a986eefdfConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-367e1dd5b4be43009c42c65e58e7ce91Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f52e6d29d3fb4a2fbdc7a4f772c95129Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f52e6d29d3fb4a2fbdc7a4f772c95129Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7ea74ea3223e4267bf22469a986eefdfConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-367e1dd5b4be43009c42c65e58e7ce91Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure described in Step 2 of Example 4, 6-bromo-1-methyl-2-naphthol (2.44 g 10.3 mmol) was coupled to ethyl 2-hydroxy-3-phenylpropanoate (3.0 g, 15 mmol) in presence of triphenylphosphine (4.17 g, 15.9 mmol) and diisopropyl azodicarboxylate (3.0 mL, 15 mmol) in benzene (65 mL). Purification by flash chromatography using 100% hexane and 1-4% ethyl acetate in hexane as eluants afforded ethyl 2-[(6-bromo-1-methyl-2-naphthyl)oxy]-3-phenylpropanoate as a transparent yellow gum (1.86 g). 1HNMR (400 MHz, DMSO-d6): δ8.1 (s, 1H), 7.9 (d, 1H, J=7.0 Hz), 7.7 (d, 1H, J=7.0 Hz), 7.6 (d, 1H, J=6.3 Hz), 7.3-7.4 (m, 4 H), 7.2-7.3 (m, 2H), 5.25 (t, 1H, J=6.3 Hz), 4.1 (q, 2H, J=7.0 Hz), 3.25-3.35 (m, 2H), 2.45 (s, 3H), and 1.1 ppm (t, 3H, J=7.0 Hz). Purification by flash chromatography
Source ID: ord-ff68eb540295489390a1de91d80ba12cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Following the procedure described in Step 2 of Example 4, 1-[2-(5-bromo-6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (2.38 g, 5.62 mmol) was coupled to ethyl 2-hydroxy-3-phenylpropanoate (1.65 g, 8.50 mmol) in presence of triphenylphosphine (2.23 g, 8.50 mmol) and diisopropylazodicarboxylate (1.7 mL, 8.5 mmol) in benzene (62 mL). Purification by HPLC, using 95% acetonitrile in water as the mobile phase, yielded ethyl 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a yellow gum (1.86 g). 1HNMR (300 MHz, DMSO-d6): δ8.45 (s, 1H), 8.25 (d, 1H, J=7.7 Hz), 8.1 (d, 1H, J=7.7 Hz), 7.95-8.1 (m, 2H), 7.85 (d, 1H, J=7.7 Hz), 7.4-7.5 (m, 5H), 7.2-7.4 (m, 3H), 5.5 (t, 1H, J=6.0 Hz), 4.1 (q, 2H, J=7.0 Hz), 2.75 (t, 2H, J=7.0 Hz), 1.45-1.6 (m, 2H), 1.05-1.25 (m, 6H), and 0.7 ppm (t, 3H, J=7.0 Hz). Purification by HPLC
Source ID: ord-bb2998887a54475ca4755f3f5173b88cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To an ice-cooled mixture of 1-[2-(6-hydroxy-2-naphthyl)-1-benzofuran-3-yl]-1-pentanone (0.620 g, 1.80 mmol), ethyl 2-hydroxy-3-phenylpropanoate (0.528 g, 2.72 mmol), triphenylphosphine (0.710 g, 2.71 mmol) in benzene (30 mL) was added, dropwise, diisopropyl azodicarboxylate (0.53 mL, 2.7 mmol) in benzene (5 mL). The mixture was stirred at room temperature for 45 minutes, poured into excess water and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Biotage apparatus) using 100% hexane and 2-3.5% ethyl acetate in hexane as eluants. The title compound was obtained as a thick yellow oil (0.670 g). Mass spectrum (+ESI, [M+H]+) m/z 521.5; 1HNMR (500 MHz, DMSO-d6): δ8.35 (s, 1H), 8.0 (t, 2H, J=7.8 Hz), 7.95 (d, 1H, J=8.6 Hz), 7.8 (dd, 1H, J=8.6 Hz and 1.7 Hz), 7.7 (d, 1H, J=8.1 Hz), 7.25-7.45 (m, 9H), 5.35 (t, 2H, J=6.5 Hz), 4.05-4.15 (m, 3H), 2.7 (t, 2H, J=7.3 Hz), 1.5-1.55 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.4 Hz). was added extracted with ethyl acetate The organic phase was washed with brine dried over anhydrous magnesium sulfate filtered concentrated The residue was purified by flash chromatography (Biotage apparatus)
Source ID: ord-fa7a13278b8f426fb803491951b97be8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-hydroxy-3-phenylpropanoic acid (2.10 g, 12.6 mmol) in ethanol (50 mL) was saturated with gaseous hydrochloric acid and allowed to stand at room temperature overnight. The reaction mixture was poured into water, neutralized with solid sodium hydrogen carbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give ethyl 2-hydroxy-3-phenylpropanoate as a peach-colored oil (2.00 g, 82%); 1HNMR (200 MHz, DMSO-d6): δ7.15-7.35 (m, 5H), 5.4-5.6 (br, 1H), 4.15-4.3 (br, 1H), 4.05 (q, 2H, J=7.3 Hz), 2.75-3.0 (m, 2H), and 1.2 ppm (t, 3H, J=7.4 Hz). extracted with ethyl acetate The organic phase was washed with brine dried over anhydrous magnesium sulfate filtered concentrated
Source ID: ord-c86034687ad043ab94958570dbcfd095PubChem References
These sources are listed in the compound's public database record.
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