No renderable structure data available
O(CCO)CCOCC=CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | Allyldiglycol |
|---|---|
| IUPAC Name | — |
| CAS Number | 15075-50-0 |
| Database ID | 84777 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
Allyldiglycol (CAS 15075-50-0) 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 84777
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b5338c0ceb40461cbacb97619863723dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-45c540df1b5a4a818637f4bfec2809f4Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of alcohol (9) (4.86 g, 33.2 mmol, 1.0 equiv.) in THF (70 mL) was carefully added NaH (60%, 1.60 g, 40.0 mmol, 1.2 equiv.) in small portions at room temperature. The reaction was then refluxed for 1 h (until H2 release ceased) then cooled to 0° C. Methyl bromoacetate (3.8 mL, 40.1 mmol, 1.2 equiv.) was then added dropwise. After 15 min at 0° C., the reaction was submitted to a EtOAc/H2O extraction. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered then evaporated under reduced pressure. Purification was achieved by distillation under high vacuum and provided 4.68 g (64%) of ester (14) as a colourless oil; bp=130-140 0° C. (0.09 Torr); 1H NMR (300 MHz, CDCl3) δ 5.91 (m, 1H), 5.28 (m, 1H), 5.18 (m, 1H), 4.17 (s, 2H), 4.02 (m, 2H), 3.75 (s, 3H), 3.75-3.58 (m, 8H); 13C NMR (75 MHz, CDCl3) δ 171.0, 134.8, 117.1, 72.3, 71.0, 70.8, 70.7, 69.5, 68.7, 51.8; IR (neat) 1754 cm−1; HRMS (ESI, m/z) calcd. for C10H19O5 (MH+) 219.1236. found 219.1227. at room temperature The reaction was then refluxed for 1 h (until H2 release ceased) the reaction was submitted to a EtOAc/H2O extraction The combined organic phases were washed with brine dried over anhydrous Na2SO4 filtered then evaporated under reduced pressure Purification was achieved by distillation under high vacuum
Source ID: ord-9608571b8d63443296377f46dec57da8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of alcohol (9) (8.77 g, 60.0 mmol, 2.2 equiv.) in THF (100 mL) was added freshly hexanes-degreased Na (0.2 g, 8.7 mmol, 0.3 equiv.) in small portions at room temperature. The reaction was then stirred at room temperature for 1 h (until the Na chunks disappeared). A solution of ethyl acrylate (2.97 mL, 27.3 mmol, 1.0 equiv.) in THF (30 mL) was then added dropwise (30 min) through an addition funnel. After 2 h at room temperature, the reaction was quenched with 10 drops of glacial acetic acid then submitted to a CHCl3/H2O extraction. The combined organic layers were dried over anhydrous MgSO4, filtered then evaporated under reduced pressure to provide crude ester (10). The latter was diluted with a 1/1 (v/v) mixture of MeOH (120 mL) and 2.5 M KOH aqueous solution (120 mL). The reaction was vigorously stirred at room temperature overnight then extracted with CHCl3. The aqueous layer was carefully acidified with concentrated (38%) HCl then extracted with CHCl3. The combined organic layers were dried over anhydrous MgSO4, filtered then evaporated under reduced pressure to provide crude acid (11). The latter (4.05 g, 18.6 mmol, 1.0 equiv.) was diluted with CH2Cl2 (120 mL) then DCC (4.25 g, 20.4 mmol, 1.1 equiv.), 2,2,2-trifluoroethanol (1.50 mL, 20.4 mmol, 1.1 equiv.) and 4-DMAP (0.23 g, 1.9 mmol, 0.1 equiv.) were successively added. The reaction was stirred at room temperature overnight then filtered through a short plug of Celite (CH2Cl2 washings). After evaporation of the filtrate under reduced pressure, the final purification was achieved by column chromatography on silica gel (Hexanes/EtOAc gradient) and provided 3.59 g (44%, 3 steps) of ester (12) as a pale yellow oil; 1H NMR (400 MHz, CDCl3) δ 5.92 (m, 1H), 5.28 (m, 1H), 5.18 (m, 1H), 4.40 (q, J=8.4 Hz, 2H), 4.03 (m, 2H), 3.79 (t, J=6.4 Hz, 2H), 3.63 (m, 8H), 2.71 (t, J=6.4 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 170.2, 134.9, 123.1 (q, J=275.7 Hz), 117.2, 72.4, 70.9, 70.8, 70.7, 69.6, 66.3, 60.5 (q, J=36.5 Hz), 34.8; IR (neat) 1760 cm−1; HRMS (ESI, m/z) calcd. for C12H20O5F3 (MH+) 301.1257. found 301.1258. the reaction was quenched with 10 drops of glacial acetic acid then submitted to a CHCl3/H2O extraction The combined organic layers were dried over anhydrous MgSO4 filtered then evaporated under reduced pressure to provide crude ester (10) then extracted with CHCl3 with concentrated (38%) HCl then extracted with CHCl3 The combined organic layers were dried over anhydrous MgSO4 filtered then evaporated under reduced pressure to provide crude acid (11) The reaction was stirred at room temperature overnight then filtered through a short plug of Celite (CH2Cl2 washings) After evaporation of the filtrate under reduced pressure the final purification
Source ID: ord-c3d697f2842f47d1ac430339ca2f9fd7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of alcohol (9) (8.77 g, 60.0 mmol, 2.2 equiv.) in THF (100 mL) was added freshly hexanes-degreased Na (0.2 g, 8.7 mmol, 0.3 equiv.) in small portions at room temperature. The reaction was then stirred at room temperature for 1 h (until the Na chunks disappeared). A solution of ethyl acrylate (2.97 mL, 27.3 mmol, 1.0 equiv.) in THF (30 mL) was then added dropwise (30 min) through an addition funnel. After 2 h at room temperature, the reaction was quenched with 10 drops of glacial acetic acid then submitted to a CHCl3/H2O extraction. The combined organic layers were dried over anhydrous MgSO4, filtered then evaporated under reduced pressure to provide crude ester (10). The latter was diluted with a 1/1 (v/v) mixture of MeOH (120 mL) and 2.5 M KOH aqueous solution (120 mL). The reaction was vigorously stirred at room temperature overnight then extracted with CHCl3. The aqueous layer was carefully acidified with concentrated (38%) HCl then extracted with CHCl3. The combined organic layers were dried over anhydrous MgSO4, filtered then evaporated under reduced pressure to provide crude acid (11). The latter (4.05 g, 18.6 mmol, 1.0 equiv.) was diluted with CH2Cl2 (120 mL) then DCC (4.25 g, 20.4 mmol, 1.1 equiv.), 2,2,2-trifluoroethanol (1.50 mL, 20.4 mmol, 1.1 equiv.) and 4-DMAP (0.23 g, 1.9 mmol, 0.1 equiv.) were successively added. The reaction was stirred at room temperature overnight then filtered through a short plug of Celite (CH2Cl2 washings). After evaporation of the filtrate under reduced pressure, the final purification was achieved by column chromatography on silica gel (Hexanes/EtOAc gradient) and provided 3.59 g (44%, 3 steps) of ester (12) as a pale yellow oil; 1H NMR (400 MHz, CDCl3) δ 5.92 (m, 1H), 5.28 (m, 1H), 5.18 (m, 1H), 4.40 (q, J=8.4 Hz, 2H), 4.03 (m, 2H), 3.79 (t, J=6.4 Hz, 2H), 3.63 (m, 8H), 2.71 (t, J=6.4 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 170.2, 134.9, 123.1 (q, J=275.7 Hz), 117.2, 72.4, 70.9, 70.8, 70.7, 69.6, 66.3, 60.5 (q, J=36.5 Hz), 34.8; IR (neat) 1760 cm−1; HRMS (ESI, m/z) calcd. for C12H20O5F3 (MH+) 301.1257. found 301.1258. the reaction was quenched with 10 drops of glacial acetic acid then submitted to a CHCl3/H2O extraction The combined organic layers were dried over anhydrous MgSO4 filtered then evaporated under reduced pressure to provide crude ester (10) then extracted with CHCl3 with concentrated (38%) HCl then extracted with CHCl3 The combined organic layers were dried over anhydrous MgSO4 filtered then evaporated under reduced pressure to provide crude acid (11) The reaction was stirred at room temperature overnight then filtered through a short plug of Celite (CH2Cl2 washings) After evaporation of the filtrate under reduced pressure the final purification
Source ID: ord-c3d697f2842f47d1ac430339ca2f9fd7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of ester (8) (9.77 g, 55.1 mmol, 1.0 equiv.) in THF (100 mL) was carefully added one portion of LAH (95%, 1.10 g, 27.5 mmol, 0.5 equiv.) at 0° C. After 30 min, another portion of LAH was carefully added and the reaction was stirred for an additional 30 min. The reaction was then carefully quenched with a Na2SO4-saturated aqueous solution. The resulting white aluminum salts were then filtered off over a short plug of Celite (EtOAc washings) and the filtrate was evaporated under reduced pressure. Purification was achieved by Kugelrohr distillation under reduced pressure and provided 7.99 g (99%) of alcohol (9) as a colorless oil; bp>200° C. (water tap vacuum). Spectroscopic data were consistent with those reported in the literature.26 1H NMR (400 MHz, CDCl3) δ 5.92 (m, 1H), 5.28 (m, 1H), 5.19 (m, 1H), 4.04 (m, 2H), 3.73 (m, 2H), 3.68 (m, 2H), 3.62 (m, 4H), 2.36 (brs, 1H). The reaction was then carefully quenched with a Na2SO4-saturated aqueous solution The resulting white aluminum salts were then filtered off over a short plug of Celite (EtOAc washings) the filtrate was evaporated under reduced pressure Purification was achieved by Kugelrohr distillation under reduced pressure
Source ID: ord-955657a80d85420a9c9e424d3cf9d91cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethylene glycol monoallyl ether was prepared by reacting allyl bromide with excess diethylene glycol in THF-NaH (tetrahydrofuran-sodium hydride). The product was obtained in 82% yield after distillation. b.p.=96-99° C./7 mmHg. The product was obtained in 82% yield after distillation
Source ID: ord-4e69885985a74b1ca4a5f8fc798f2882Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b5338c0ceb40461cbacb97619863723dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-45c540df1b5a4a818637f4bfec2809f4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Diethylene glycol monoallyl ether was prepared by reacting allyl bromide with excess diethylene glycol in THF-NaH (tetrahydrofuran-sodium hydride). The product was obtained in 82% yield after distillation. b.p.=96-99° C./7 mmHg. The product was obtained in 82% yield after distillation
Source ID: ord-4e69885985a74b1ca4a5f8fc798f2882Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of alcohol (9) (4.86 g, 33.2 mmol, 1.0 equiv.) in THF (70 mL) was carefully added NaH (60%, 1.60 g, 40.0 mmol, 1.2 equiv.) in small portions at room temperature. The reaction was then refluxed for 1 h (until H2 release ceased) then cooled to 0° C. Methyl bromoacetate (3.8 mL, 40.1 mmol, 1.2 equiv.) was then added dropwise. After 15 min at 0° C., the reaction was submitted to a EtOAc/H2O extraction. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered then evaporated under reduced pressure. Purification was achieved by distillation under high vacuum and provided 4.68 g (64%) of ester (14) as a colourless oil; bp=130-140 0° C. (0.09 Torr); 1H NMR (300 MHz, CDCl3) δ 5.91 (m, 1H), 5.28 (m, 1H), 5.18 (m, 1H), 4.17 (s, 2H), 4.02 (m, 2H), 3.75 (s, 3H), 3.75-3.58 (m, 8H); 13C NMR (75 MHz, CDCl3) δ 171.0, 134.8, 117.1, 72.3, 71.0, 70.8, 70.7, 69.5, 68.7, 51.8; IR (neat) 1754 cm−1; HRMS (ESI, m/z) calcd. for C10H19O5 (MH+) 219.1236, found 219.1227. at room temperature The reaction was then refluxed for 1 h (until H2 release ceased) the reaction was submitted to a EtOAc/H2O extraction The combined organic phases were washed with brine dried over anhydrous Na2SO4 filtered then evaporated under reduced pressure Purification was achieved by distillation under high vacuum
Source ID: ord-df7cf8b013e5482aa7098e89ff25e6a7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of alcohol (9) (8.77 g, 60.0 mmol, 2.2 equiv.) in THF (100 mL) was added freshly hexanes-degreased Na (0.2 g, 8.7 mmol, 0.3 equiv.) in small portions at room temperature. The reaction was then stirred at room temperature for 1 h (until the Na chunks disappeared). A solution of ethyl acrylate (2.97 mL, 27.3 mmol, 1.0 equiv.) in THF (30 mL) was then added dropwise (30 min) through an addition funnel. After 2 h at room temperature, the reaction was quenched with 10 drops of glacial acetic acid then submitted to a CHCl3/H2O extraction. The combined organic layers were dried over anhydrous MgSO4, filtered then evaporated under reduced pressure to provide crude ester (10). The latter was diluted with a 1/1 (v/v) mixture of MeOH (120 mL) and 2.5 M KOH aqueous solution (120 mL). The reaction was vigorously stirred at room temperature overnight then extracted with CHCl3. The aqueous layer was carefully acidified with concentrated (38%) HCl then extracted with CHCl3. The combined organic layers were dried over anhydrous MgSO4, filtered then evaporated under reduced pressure to provide crude acid (11). The latter (4.05 g, 18.6 mmol, 1.0 equiv.) was diluted with CH2Cl2 (120 mL) then DCC (4.25 g, 20.4 mmol, 1.1 equiv.), 2,2,2-trifluoroethanol (1.50 mL, 20.4 mmol, 1.1 equiv.) and 4-DMAP (0.23 g, 1.9 mmol, 0.1 equiv.) were successively added. The reaction was stirred at room temperature overnight then filtered through a short plug of Celite (CH2Cl2 washings). After evaporation of the filtrate under reduced pressure, the final purification was achieved by column chromatography on silica gel (Hexanes/EtOAc gradient) and provided 3.59 g (44%, 3 steps) of ester (12) as a pale yellow oil; 1H NMR (400 MHz, CDCl3) δ 5.92 (m, 1H), 5.28 (m, 1H), 5.18 (m, 1H), 4.49 (q, J=8.4 Hz, 2H), 4.03 (m, 2H), 3.79 (t, J=6.4 Hz, 2H), 3.63 (m, 8H), 2.71 (t, J=6.4 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 170.2, 134.9, 123.1 (q, J=275.7 Hz), 117.2, 72.4, 70.9, 70.8, 70.7, 69.6, 66.3, 60.5 (q, J=36.5 Hz), 34.8; IR (neat) 1760 cm−1; HRMS (ESI, m/z) calcd. for C12H20O5F3 (MH+) 301.1257, found 301.1258. the reaction was quenched with 10 drops of glacial acetic acid then submitted to a CHCl3/H2O extraction The combined organic layers were dried over anhydrous MgSO4 filtered then evaporated under reduced pressure to provide crude ester (10) then extracted with CHCl3 with concentrated (38%) HCl then extracted with CHCl3 The combined organic layers were dried over anhydrous MgSO4 filtered then evaporated under reduced pressure to provide crude acid (11) The reaction was stirred at room temperature overnight then filtered through a short plug of Celite (CH2Cl2 washings) After evaporation of the filtrate under reduced pressure the final purification
Source ID: ord-36c70b18d22747bd872c438411438226PubChem References
These sources are listed in the compound's public database record.
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