No renderable structure data available
CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1,3-Dioctanoylglycerol |
|---|---|
| IUPAC Name | — |
| CAS Number | 1429-66-9 |
| Database ID | 150911 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1,3-Dioctanoylglycerol (CAS 1429-66-9) 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 150911
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-47940f2314e24ababfd8cd724d6ff707Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9326f1df22854a1db3e7510e2f1904b6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-hydroxy-3-octanoyloxypropyl octanoate (5.0 g.) in ether (30 ml.) was stirred with triethylamine (2.04 ml.) and glutaric anhydride (1.66 g.) for 3.5 hours. Further glutaric anhydride (0.8 g.) was then added together with triethylamine (1.0 ml.). This mixture was heated under reflux until no further starting octanoate could be detected by thin layer chromatography (silica: methylene chloride). The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.), then with water (2×20 ml.), dried (MgSO4) and evaporated to give 2-octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate as an oil (6.62 g.); NMR (CDCl3): 0.9 (6H, t, CH3), 1.1-2.1 (22H, m, CH2), 2.4 (8H, m, CH2CO), 4.0-4.4 (4H,m, CH2O), 5.1-5.4 (1H, br.t, CHO), 9.6 (1H, br.s, CO2H)ppm. Mass spectrum (major diagnostic peaks based on M=458, using chemical ionisation techniques): m/e 476 (M+NH4), 360 (M +NH4 --HO2C.(CH2)3.CO2H) This mixture was heated under reflux until The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.) with water (2×20 ml.), dried (MgSO4) evaporated
Source ID: ord-7f45509cc2254f9f8333e2ba5f1b0838Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-hydroxy-3-octanoyloxypropyl octanoate (5.0 g.) in ether (30 ml.) was stirred with triethylamine (2.04 ml.) and glutaric anhydride (1.66 g.) for 3.5 hours. Further glutaric anhydride (0.8 g.) was then added together with triethylamine (1.0 ml.). This mixture was heated under reflux until no further starting octanoate could be detected by thin layer chromatography (silica: methylene chloride). The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.), then with water (2×20 ml.), dried (MgSO4) and evaporated to give 2-octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate as an oil (6.62 g.); NMR (CDCl3): 0.9 (6H, t, CH3), 1.1-2.1 (22H, m, CH2), 2.4 (8H, m, CH2CO), 4.0-4.4 (4H,m, CH2O), 5.1-5.4 (1H, br.t, CHO), 9.6 (1H, br.s, CO2H)ppm. Mass spectrum (major diagnostic peaks based on M=458, using chemical ionisation techniques): m/e 476 (M+NH4), 360 (M +NH4 --HO2C.(CH2)3.CO2H) This mixture was heated under reflux until The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.) with water (2×20 ml.), dried (MgSO4) evaporated
Source ID: ord-7f45509cc2254f9f8333e2ba5f1b0838Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using a similar procedure to that described in Example 6, but using 5-chloro-2-(2,4-dichlorophenoxy)phenol, adipoyl dichloride and 2-hydroxy-3-octanoyloxypropyl octanoate as starting materials, there was obtained 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipate as an oil in 33% yield; NMR (CDCL3): 0.85 (6H, br.s, CH3), 1.25+1.65 (24H, br.s, CH2), 2.3 (8H, m, COCH2), 4.2 (4H, m, OCH2), 5.25 (1H, m, CH), 6.6-7.5 (6H, complex, aromatic H)ppm.
Source ID: ord-962d4d809c1646448aff1daaf2ff3aaeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using a similar procedure to that described in Example 6, but using 5-chloro-2-(2,4-dichlorophenoxy)phenol, adipoyl dichloride and 2-hydroxy-3-octanoyloxypropyl octanoate as starting materials, there was obtained 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipate as an oil in 33% yield; NMR (CDCL3): 0.85 (6H, br.s, CH3), 1.25+1.65 (24H, br.s, CH2), 2.3 (8H, m, COCH2), 4.2 (4H, m, OCH2), 5.25 (1H, m, CH), 6.6-7.5 (6H, complex, aromatic H)ppm.
Source ID: ord-962d4d809c1646448aff1daaf2ff3aaeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-hydroxy-3-octanoyloxy-propyl octanoate (7.0 g.) and pyridine (1.5 g.) in chloroform (100 ml.) was treated dropwise at 0°-5° C. with a solution of 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-chloroformylbutyrate (A) (8.4 g.). The reaction mixture was then stirred at ambient temperature for 1 hour and diluted with ether (300 ml.) and water (200 ml). The organic phase was separated, washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.), and then dried (MgSO4) and evaporated. The residual oil was purified by chromatography on silica gel (50 g.) using a mixture of petrol 60-80 and ether (70:30 v/v) as eluant to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate as an oil.(9.1 g.); NMR (CDCl3): 0.9 (6H, t J=4.0 Hz, CH3), 1.1-7 (20H, complex m, CH2 ), 1.98 (2H,m, CH2), 2.2-2.7 (8H, complex, CO.CH2), 4.0-4.5 (4H,complex, CH2O), 5.25 (1H, br.t J=4.5 Hz, CH), 6.75-7.55 (6H,complex, aromatic H)ppm; mass spectrum (major diagnostic peaks): m/e 585 (16%) [M-0.CO(CH2)6CH3 ], 441. (21%), 385 (12%), 327 (100%), 288 (10%), 201 (10%), 127 (46%). The organic phase was separated washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.) dried (MgSO4) evaporated The residual oil was purified by chromatography on silica gel (50 g.) a mixture of petrol 60-80 and ether (70:30 v/v) as eluant
Source ID: ord-41eb8bcf7b8147b19dc74876dee06d48Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-hydroxy-3-octanoyloxy-propyl octanoate (7.0 g.) and pyridine (1.5 g.) in chloroform (100 ml.) was treated dropwise at 0°-5° C. with a solution of 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-chloroformylbutyrate (A) (8.4 g.). The reaction mixture was then stirred at ambient temperature for 1 hour and diluted with ether (300 ml.) and water (200 ml). The organic phase was separated, washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.), and then dried (MgSO4) and evaporated. The residual oil was purified by chromatography on silica gel (50 g.) using a mixture of petrol 60-80 and ether (70:30 v/v) as eluant to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate as an oil.(9.1 g.); NMR (CDCl3): 0.9 (6H, t J=4.0 Hz, CH3), 1.1-7 (20H, complex m, CH2 ), 1.98 (2H,m, CH2), 2.2-2.7 (8H, complex, CO.CH2), 4.0-4.5 (4H,complex, CH2O), 5.25 (1H, br.t J=4.5 Hz, CH), 6.75-7.55 (6H,complex, aromatic H)ppm; mass spectrum (major diagnostic peaks): m/e 585 (16%) [M-0.CO(CH2)6CH3 ], 441. (21%), 385 (12%), 327 (100%), 288 (10%), 201 (10%), 127 (46%). The organic phase was separated washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.) dried (MgSO4) evaporated The residual oil was purified by chromatography on silica gel (50 g.) a mixture of petrol 60-80 and ether (70:30 v/v) as eluant
Source ID: ord-41eb8bcf7b8147b19dc74876dee06d48Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-hydroxy-3-octanoyloxypropyl octanoate (5.0 g.) in ether (30 ml.) was stirred with triethylamine (2.04 ml.) and glutaric anhydride (1.66 g.) for 3.5 hours. Further glutaric anhydride (0.8 g.) was then added together with triethylamine (1.0 ml.). This mixture was heated under reflux until no further starting octanoate could be detected by thin layer chromatography (silica: methylene chloride). The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.), then with water (2×20 ml.), dried (MgSO4) and evaporated to give 2-octanoyloxy-1-(octanoyloxymethyl)ethyl hydrogen glutarate as an oil (6.62 g.); NMR (CDCl3): 0.9 (6H, t, CH3), 1.1-2.1 (22H, m, CH2), 2.4 (8H, m, CH2CO), 4.0-4.4 (4H,m, CH2O), 5.1-5.4 (1H, br.t, CHO), 9.6 (1H, br.s, CO2H)ppm. Mass spectrum (major diagnostic peaks based on M=458, using chemical ionisation techniques): m/e 476 (M+NH4), 360 (M +NH4 --HO2C.(CH2)3.CO2H) This mixture was heated under reflux until The cooled reaction mixture was washed with 1M hydrochloric acid (2×20 ml.) with water (2×20 ml.), dried (MgSO4) evaporated
Source ID: ord-7f45509cc2254f9f8333e2ba5f1b0838Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Using a similar procedure to that described in Example 6, but using 5-chloro-2-(2,4-dichlorophenoxy)phenol, adipoyl dichloride and 2-hydroxy-3-octanoyloxypropyl octanoate as starting materials, there was obtained 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl adipate as an oil in 33% yield; NMR (CDCL3): 0.85 (6H, br.s, CH3), 1.25+1.65 (24H, br.s, CH2), 2.3 (8H, m, COCH2), 4.2 (4H, m, OCH2), 5.25 (1H, m, CH), 6.6-7.5 (6H, complex, aromatic H)ppm.
Source ID: ord-962d4d809c1646448aff1daaf2ff3aaeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 2-hydroxy-3-octanoyloxy-propyl octanoate (7.0 g.) and pyridine (1.5 g.) in chloroform (100 ml.) was treated dropwise at 0°-5° C. with a solution of 5-chloro-2-(2,4-dichlorophenoxy)phenyl 4-chloroformylbutyrate (A) (8.4 g.). The reaction mixture was then stirred at ambient temperature for 1 hour and diluted with ether (300 ml.) and water (200 ml). The organic phase was separated, washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.), and then dried (MgSO4) and evaporated. The residual oil was purified by chromatography on silica gel (50 g.) using a mixture of petrol 60-80 and ether (70:30 v/v) as eluant to give 5-chloro-2-(2,4-dichlorophenoxy)phenyl 2-octanoyloxy-1-(octanoyloxymethyl)ethyl glutarate as an oil.(9.1 g.); NMR (CDCl3): 0.9 (6H, t J=4.0 Hz, CH3), 1.1-7 (20H, complex m, CH2 ), 1.98 (2H,m, CH2), 2.2-2.7 (8H, complex, CO.CH2), 4.0-4.5 (4H,complex, CH2O), 5.25 (1H, br.t J=4.5 Hz, CH), 6.75-7.55 (6H,complex, aromatic H)ppm; mass spectrum (major diagnostic peaks): m/e 585 (16%) [M-0.CO(CH2)6CH3 ], 441. (21%), 385 (12%), 327 (100%), 288 (10%), 201 (10%), 127 (46%). The organic phase was separated washed successively with 2M hydrochloric acid (50 ml.), saturated sodium bicarbonate solution (3×50 ml.) dried (MgSO4) evaporated The residual oil was purified by chromatography on silica gel (50 g.) a mixture of petrol 60-80 and ether (70:30 v/v) as eluant
Source ID: ord-41eb8bcf7b8147b19dc74876dee06d48Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-47940f2314e24ababfd8cd724d6ff707PubChem References
These sources are listed in the compound's public database record.
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