No renderable structure data available
BrC1=CC=CC=C1CC(C(=O)OCC)C(=O)OCCChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | Propanedioic acid, [(2-bromophenyl)methyl]-, diethyl ester |
|---|---|
| IUPAC Name | — |
| CAS Number | 66192-11-8 |
| Database ID | 12853296 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
Propanedioic acid, [(2-bromophenyl)methyl]-, diethyl ester (CAS 66192-11-8) 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 12853296
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-bdaa4c18739d4937a91b98e52ee32039Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of diethyl(2-bromobenzyl)propan-1,3-dioate (11.87 g, 30 mmol) with 1-tridecyne (11.10 g, 45 mmol) as described in example 3 gave 3.89 g (29%) of the title compound as a pale yellow oil after chromatography. It had νmax (film) 1735, 1755, 2840, 2920 cm-1 ; δ(CDCl3) 0.87 (3H, distorted t, terminal CH3), 1.08 (6H, t, J 7 Hz, ester CH3), 1.28 (18H, m, alkylene chain), 2.42 (2H, t, J 6 Hz, C≡C--CH2), 3.31 (2H, d, J 7.5 Hz, ArCH2), 3.90 (1H, t, J 7.5 Hz, methine H), 4.12 (4H, q, J 7.5 Hz, ester CH2), 7.15 (3H, m, aromatics), 7.36 (1H, m, aromatic). M+ 428.2928 (C27H40O4 requires; 428.2926).
Source ID: ord-bb4da2c74b46483b9aa5adca68a6d049Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of diethyl(2-bromobenzyl)propan-1,3-dioate (11.87 g, 30 mmol) with 1-tridecyne (11.10 g, 45 mmol) as described in example 3 gave 3.89 g (29%) of the title compound as a pale yellow oil after chromatography. It had νmax (film) 1735, 1755, 2840, 2920 cm-1 ; δ(CDCl3) 0.87 (3H, distorted t, terminal CH3), 1.08 (6H, t, J 7 Hz, ester CH3), 1.28 (18H, m, alkylene chain), 2.42 (2H, t, J 6 Hz, C≡C--CH2), 3.31 (2H, d, J 7.5 Hz, ArCH2), 3.90 (1H, t, J 7.5 Hz, methine H), 4.12 (4H, q, J 7.5 Hz, ester CH2), 7.15 (3H, m, aromatics), 7.36 (1H, m, aromatic). M+ 428.2928 (C27H40O4 requires; 428.2926).
Source ID: ord-bb4da2c74b46483b9aa5adca68a6d049Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl malonate (77 g, 0.48 mol) was added to a stirred solution of sodium (10.2 g, 0.425 mol) in ethanol (800 ml) followed by 2-bromobenzyl bromide (100 g, 0.40 mol). Sodium bromide began to separate towards the end of the addition and the mixture became warm. The reaction was completed by refluxing on a steam bath for 3 hours and then cooling overnight. The bulk of the solvent was removed in vacuo, water was added and the product extracted into ether. After drying (CaCl2) and evaporation the product was distilled to give 93.28 g (71%) of material of bp0.2 130° C. (lit bp0.004 115°-120° C., F. G. Holliman and F. G. Mann J. Chem. Soc. 9, [1960]). to separate towards the end of the addition the mixture became warm by refluxing on a steam bath for 3 hours cooling overnight The bulk of the solvent was removed in vacuo, water was added the product extracted into ether After drying (CaCl2) and evaporation the product was distilled
Source ID: ord-37e19e9937584beea98ab370d4bf0d4bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl malonate (77 g, 0.48 mol) was added to a stirred solution of sodium (10.2 g, 0.425 mol) in ethanol (800 ml) followed by 2-bromobenzyl bromide (100 g, 0.40 mol). Sodium bromide began to separate towards the end of the addition and the mixture became warm. The reaction was completed by refluxing on a steam bath for 3 hours and then cooling overnight. The bulk of the solvent was removed in vacuo, water was added and the product extracted into ether. After drying (CaCl2) and evaporation the product was distilled to give 93.28 g (71%) of material of bp0.2 130° C. (lit bp0.004 115°-120° C., F. G. Holliman and F. G. Mann J. Chem. Soc. 9, [1960]). to separate towards the end of the addition the mixture became warm by refluxing on a steam bath for 3 hours cooling overnight The bulk of the solvent was removed in vacuo, water was added the product extracted into ether After drying (CaCl2) and evaporation the product was distilled
Source ID: ord-37e19e9937584beea98ab370d4bf0d4bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of diethyl(2-bromobenzyl)propan-1,3-dioate (11.87 g, 30 mmol) with 1-tridecyne (11.10 g, 45 mmol) as described in example 3 gave 3.89 g (29%) of the title compound as a pale yellow oil after chromatography. It had νmax (film) 1735, 1755, 2840, 2920 cm-1 ; δ(CDCl3) 0.87 (3H, distorted t, terminal CH3), 1.08 (6H, t, J 7 Hz, ester CH3), 1.28 (18H, m, alkylene chain), 2.42 (2H, t, J 6 Hz, C≡C--CH2), 3.31 (2H, d, J 7.5 Hz, ArCH2), 3.90 (1H, t, J 7.5 Hz, methine H), 4.12 (4H, q, J 7.5 Hz, ester CH2), 7.15 (3H, m, aromatics), 7.36 (1H, m, aromatic). M+ 428.2928 (C27H40O4 requires; 428.2926).
Source ID: ord-bb4da2c74b46483b9aa5adca68a6d049Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl malonate (77 g, 0.48 mol) was added to a stirred solution of sodium (10.2 g, 0.425 mol) in ethanol (800 ml) followed by 2-bromobenzyl bromide (100 g, 0.40 mol). Sodium bromide began to separate towards the end of the addition and the mixture became warm. The reaction was completed by refluxing on a steam bath for 3 hours and then cooling overnight. The bulk of the solvent was removed in vacuo, water was added and the product extracted into ether. After drying (CaCl2) and evaporation the product was distilled to give 93.28 g (71%) of material of bp0.2 130° C. (lit bp0.004 115°-120° C., F. G. Holliman and F. G. Mann J. Chem. Soc. 9, [1960]). to separate towards the end of the addition the mixture became warm by refluxing on a steam bath for 3 hours cooling overnight The bulk of the solvent was removed in vacuo, water was added the product extracted into ether After drying (CaCl2) and evaporation the product was distilled
Source ID: ord-37e19e9937584beea98ab370d4bf0d4bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-bdaa4c18739d4937a91b98e52ee32039Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 4-neck 2 litre round bottom flask with equipped with a reflux condenser, thermometer and stirrer, is charged with 230 g (0.70 mol) of 2-(2-Bromo-benzyl)-malonic acid diethyl ester and placed in an oil bath. A solution of 225.8 g (4.02 mol) potassium hydroxide in 225 ml water is slowly added with stirring. The reaction temperature is carefully monitored and the addition of the potassium hydroxide solution is interrupted as soon as a significantly exothermic reaction starts. The temperature may rise up to 80° C. The remaining potassium hydroxide solution is added as soon as the initial reaction starts to subside. It may happen that no change in temperature is observed while adding the potassium hydroxide solution. If this happens, the reaction mixture is carefully and slowly heated to 80° C. The exothermic reaction may suddenly start. As soon as the initial reaction starts to subside, the reaction mixture is heated to 100° C. and stirred for 6 h at this temperature. A 4-neck 2 litre round bottom flask with equipped with a reflux condenser placed in an oil bath soon as a significantly exothermic reaction may rise up to 80° C reaction The exothermic reaction As soon as the initial reaction the reaction mixture is heated to 100° C. stirred for 6 h at this temperature
Source ID: ord-359e73b3e02149cd9be0f54c9a54e954Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Reaction of diethyl(2-bromobenzyl)propan-1,3-dioate (11.87 g, 30 mmol) with 1-tridecyne (11.10 g, 45 mmol) as described in example 3 gave 3.89 g (29%) of the title compound as a pale yellow oil after chromatography. It had νmax (film) 1735, 1755, 2840, 2920 cm-1 ; δ(CDCl3) 0.87 (3H, distorted t, terminal CH3), 1.08 (6H, t, J 7 Hz, ester CH3), 1.28 (18H, m, alkylene chain), 2.42 (2H, t, J 6 Hz, C≡C--CH2), 3.31 (2H, d, J 7.5 Hz, ArCH2), 3.90 (1H, t, J 7.5 Hz, methine H), 4.12 (4H, q, J 7.5 Hz, ester CH2), 7.15 (3H, m, aromatics), 7.36 (1H, m, aromatic). M+ 428.2928 (C27H40O4 requires; 428.2926).
Source ID: ord-bb4da2c74b46483b9aa5adca68a6d049Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethyl malonate (77 g, 0.48 mol) was added to a stirred solution of sodium (10.2 g, 0.425 mol) in ethanol (800 ml) followed by 2-bromobenzyl bromide (100 g, 0.40 mol). Sodium bromide began to separate towards the end of the addition and the mixture became warm. The reaction was completed by refluxing on a steam bath for 3 hours and then cooling overnight. The bulk of the solvent was removed in vacuo, water was added and the product extracted into ether. After drying (CaCl2) and evaporation the product was distilled to give 93.28 g (71%) of material of bp0.2 130° C. (lit bp0.004 115°-120° C., F. G. Holliman and F. G. Mann J. Chem. Soc. 9, [1960]). to separate towards the end of the addition the mixture became warm by refluxing on a steam bath for 3 hours cooling overnight The bulk of the solvent was removed in vacuo, water was added the product extracted into ether After drying (CaCl2) and evaporation the product was distilled
Source ID: ord-37e19e9937584beea98ab370d4bf0d4bPubChem References
These sources are listed in the compound's public database record.
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