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CC1(COC(OC1)CCC=O)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-(5,5-dimethyl-1,3-dioxan-2-yl)propanal |
|---|---|
| IUPAC Name | — |
| CAS Number | 58697-03-3 |
| Database ID | 93882 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-(5,5-dimethyl-1,3-dioxan-2-yl)propanal (CAS 58697-03-3) 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 93882
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-c51fcf9ceac74bd49458ec21d332cb0fConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0b0a5b2581fd43ff8950e91a5b9d8a1bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-98849a3a9d3e48c78c7bda935377a396Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c51fcf9ceac74bd49458ec21d332cb0fConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Fluorophenyl magnesium bromide (8.7 ml, 2M solution in ether, 17.44 mmol) was added to a solution of 5,5-dimethyl-1,3-dioxane-2-propanal (2 g, 11.62 mmol) (Step 2) in THF (50 ml) at −70° C. After stirring at −70° C. for 2 hr, the reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic fractions were combined and washed successively with water and brine. After drying (MgSO4), filtration and concentration, the crude compound (3.5 g) was chromatographed to give α-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-propanol (2.73 g) as a white solid: mp (DSC) 84° C. Anal Calc'd. for C15H21FO3: C, 67.14; H, 7.89. Found: C, 67.18; H, 7.98. the reaction mixture was warmed to room temperature stirred overnight The reaction was quenched with water extracted with ethyl acetate washed successively with water and brine After drying (MgSO4), filtration and concentration the crude compound (3.5 g) was chromatographed
Source ID: ord-c245a4b0bff340d4893cba7486dbe63cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: DMSO (10.2 ml, 0.14 mol) was added to a solution of oxalyl chloride (5.5 ml, 63.2 mmol) in methylene chloride (25 ml) at −78° C. After stirring for 15 min, a solution of 5,5-dimethyl-1,3-dioxane-2-propanol (Step 1) (10 g, 57.5 mmol) in methylene chloride (100 ml) was added over 10 min. The reaction was stirred for 1 hr and triethylamine (40 ml, 0.2 mol) was added. After stirring at −70° C. for 1 hr, the reaction mixture was warmed to room temperature and stirred for 2 hr. The reaction was quenched with water and extracted with methylene chloride. The organic fractions were washed with aqueous sodium bicarbonate and brine. After drying (Na2SO4), filtration and concentration, the crude compound was chromatographed (silica gel, hexane/ethyl acetate 7/3) to give 5,5-dimethyl-1,3-dioxane-2-propanal (6.1 g, 61%) as a colorless liquid: Anal Calc'd. for C9H16O3 0.2H2O: C, 61.48; H, 9.40. Found: C, 61.46; H, 9.24. The reaction was stirred for 1 hr After stirring at −70° C. for 1 hr stirred for 2 hr The reaction was quenched with water extracted with methylene chloride The organic fractions were washed with aqueous sodium bicarbonate and brine After drying (Na2SO4), filtration and concentration the crude compound was chromatographed (silica gel, hexane/ethyl acetate 7/3)
Source ID: ord-42f5453761704efcbab0d2cd61432de9Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Fluorophenyl magnesium bromide (8.7 ml, 2M solution in ether, 17.44 mmol) was added to a solution of 5,5-dimethyl-1,3-dioxane-2-propanal (2 g, 11.62 mmol) (Step 2) in THF (50 ml) at −70° C. After stirring at −70° C. for 2 hr, the reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic fractions were combined and washed successively with water and brine. After drying (MgSO4), filtration and concentration, the crude compound (3.5 g) was chromatographed to give α-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-propanol (2.73 g) as a white solid: mp (DSC) 84° C. Anal Calc'd. for C15H21FO3: C, 67.14; H, 7.89. Found: C, 67.18; H, 7.98. the reaction mixture was warmed to room temperature stirred overnight The reaction was quenched with water extracted with ethyl acetate washed successively with water and brine After drying (MgSO4), filtration and concentration the crude compound (3.5 g) was chromatographed
Source ID: ord-c245a4b0bff340d4893cba7486dbe63cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: DMSO (10.2 ml, 0.14 mol) was added to a solution of oxalyl chloride (5.5 ml, 63.2 mmol) in methylene chloride (25 ml) at −78° C. After stirring for 15 min, a solution of 5,5-dimethyl-1,3-dioxane-2-propanol (Step 1) (10 g, 57.5 mmol) in methylene chloride (100 ml) was added over 10 min. The reaction was stirred for 1 hr and triethylamine (40 ml, 0.2 mol) was added. After stirring at −70° C. for 1 hr, the reaction mixture was warmed to room temperature and stirred for 2 hr. The reaction was quenched with water and extracted with methylene chloride. The organic fractions were washed with aqueous sodium bicarbonate and brine. After drying (Na2SO4), filtration and concentration, the crude compound was chromatographed (silica gel, hexane/ethyl acetate 7/3) to give 5,5-dimethyl-1,3-dioxane-2-propanal (6.1 g, 61%) as a colorless liquid: Anal Calc'd. for C9H16O3 0.2H2O: C, 61.48; H, 9.40. Found: C, 61.46; H, 9.24. The reaction was stirred for 1 hr After stirring at −70° C. for 1 hr stirred for 2 hr The reaction was quenched with water extracted with methylene chloride The organic fractions were washed with aqueous sodium bicarbonate and brine After drying (Na2SO4), filtration and concentration the crude compound was chromatographed (silica gel, hexane/ethyl acetate 7/3)
Source ID: ord-42f5453761704efcbab0d2cd61432de9Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-98849a3a9d3e48c78c7bda935377a396Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Fluorophenyl magnesium bromide (8.7 ml, 2M solution in ether, 17.44 mmol) was added to a solution of 5,5-dimethyl-1,3-dioxane-2-propanal (2 g, 11.62 mmol) (Step 2) in THF (50 ml) at −70° C. After stirring at −70° C. for 2 hr, the reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic fractions were combined and washed successively with water and brine. After drying (MgSO4), filtration and concentration, the crude compound (3.5 g) was chromatographed to give α-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-propanol (2.73 g) as a white solid: mp (DSC) 84° C. Anal Calc'd. for C15H21FO3: C, 67.14; H, 7.89. Found: C, 67.18; H, 7.98. the reaction mixture was warmed to room temperature stirred overnight The reaction was quenched with water extracted with ethyl acetate washed successively with water and brine After drying (MgSO4), filtration and concentration the crude compound (3.5 g) was chromatographed
Source ID: ord-ddbc1d924e834ee7925edf1626573a6aConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Fluorophenyl magnesium bromide (8.7 ml, 2M solution in ether, 17.44 mmol) was added to a solution of 5,5-dimethyl-1,3-dioxane-2-propanal (2 g, 11.62 mmol) (Step 2) in THF (50 ml) at −70° C. After stirring at −70° C. for 2 hr, the reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic fractions were combined and washed successively with water and brine. After drying (MgSO4), filtration and concentration, the crude compound (3.5 g) was chromatographed to give α-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-propanol (2.73 g) as a white solid: mp (DSC) 84° C. Anal Calc'd. for C15H21FO3: C, 67.14; H, 7.89. Found: C, 67.18; H, 7.98. the reaction mixture was warmed to room temperature stirred overnight The reaction was quenched with water extracted with ethyl acetate washed successively with water and brine After drying (MgSO4), filtration and concentration the crude compound (3.5 g) was chromatographed
Source ID: ord-ddbc1d924e834ee7925edf1626573a6aConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Fluorophenyl magnesium bromide (8.7 ml, 2M solution in ether, 17.44 mmol) was added to a solution of 5,5-dimethyl-1,3-dioxane-2-propanal (2 g, 11.62 mmol) (Step 2) in THF (50 ml) at −70° C. After stirring at −70° C. for 2 hr, the reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic fractions were combined and washed successively with water and brine. After drying (MgSO4), filtration and concentration, the crude compound (3.5 g) was chromatographed to give α-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-propanol (2.73 g) as a white solid: mp (DSC) 84° C. Anal Calc'd. for C15H21FO3: C, 67.14; H, 7.89. Found: C, 67.18; H, 7.98. the reaction mixture was warmed to room temperature stirred overnight The reaction was quenched with water extracted with ethyl acetate washed successively with water and brine After drying (MgSO4), filtration and concentration the crude compound (3.5 g) was chromatographed
Source ID: ord-ddbc1d924e834ee7925edf1626573a6aPubChem References
These sources are listed in the compound's public database record.
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