No renderable structure data available
CC(C)(CCC=O)OCChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-methoxy-4-methylpentanal |
|---|---|
| IUPAC Name | — |
| CAS Number | 127426-79-3 |
| Database ID | 11829474 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-methoxy-4-methylpentanal (CAS 127426-79-3) 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 11829474
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-c5f690b493874b5a8a198500715b0182Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 4-methoxy-4-methylpentanal (60 g, 0.46 mol) and ethyl acetoacetate (156 g, 1.2 mol) at 5° C. was added a 21% solution of piperidine in ethanol (4.1 mL). Further additions (4×18 mL) of the piperidine solution were made at about 24 hour intervals. The mixture was heated at reflux for 7 hours and concentrated to about 200 mL volume. Methanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added and the resulting mixture was heated at reflux 16 hours. Workup gave 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-one bp0.1 135°-140° C. (69.2 g); NMR(CDCl3)δ1.2(s,6H), 0.9-1.6(m,5H), 1.9(s,3H), 5.9(brs,1H); IR(neat) 2975, 2930, 1675, 1640, 1380, 1080 cm-1 ; MS(m/e) 43, 73, 81, 109, 122, 163, 196. The mixture was heated at reflux for 7 hours concentrated to about 200 mL volume Methanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added the resulting mixture was heated at reflux 16 hours
Source ID: ord-b05b65604c98438ab94b09ec1a6e2082Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1,1,4-trimethoxy-4-methylpentane (3.2 g, 0.018 mol), tetrahydrofuran (100 mL), water (10 mL) and oxalic acid (1.0 g, 0.022 mol) was heated at reflux for 40 hours. Workup provided 4-methoxy-4-methylpentanal (2.0 g). was heated at reflux for 40 hours
Source ID: ord-9c9deb43c749470a8a0077035bfe0b2bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred, cooled (-65° C.) mixture of 2,6-dimethyl-2-methoxyhept-5-ene (125 g, 1.25 mol), methylene chloride (500 mL) and methanol (500 mL) was treated with a gas stream enriched with ozone. Upon the appearance of a blue color pure oxygen was passed through the mixture followed by nitrogen. Dimethyl sulfide (88 mL, 1.4 mol) was added and the mixture was allowed to stand 16 hours at 25° C. Upon workup 4-methoxy-4-methylpentanal was obtained, bp30 85°-87° C. (64.4 g); NMR(CDCl3)δ1.2(s,6H), 1.9(t,2H), 2.5(m,2H), 3.2(s,3H), 9.8(t,1H); IR(neat) 2975, 2825, 2725, 1730, 1470, 1370, 1090 cm-1 ; MS(m/e) 43, 73, 83, 115. A stirred, cooled was treated with a gas stream
Source ID: ord-db48de3f92a1469e990c4d70e4c0bf84Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 4-methoxy-4-methylpentanal (60 g, 0.46 mol) and ethyl acetoacetate (156 g, 1.2 mol) at 5~C was added a 21% solution of piperidine in ethanol (4.1 mL). Further additions (4×18 mL) of the piperidine solution were made at about 24 hour intervals. The mixture was heated at reflux for 7 hours and concentrated to about 200 mL volume. Methanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added and the resulting mixture was heated at reflux 16 hours. Workup gave 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-one bp0.1 135-140 ~C (69.2 g); NMR(CDC13)δ 1.2(s,6H), 0.9-1.6(m,5H), 1.9(s,3H), 5.9(brs,1H); IR(neat) 2975, 2930, 1675, 1640, 1380, 1080 cm-1 ; MS(m/e) 43, 73, 81, 109, 122, 163, 196. The mixture was heated at reflux for 7 hours concentrated to about 200 mL volume Methanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added the resulting mixture was heated at reflux 16 hours
Source ID: ord-8f96f965d6274cad8e0b59ab8feae3beConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1,1,4-trimethoxy-4-methylpentane (3.2 g, 0.018 mol), tetrahydrofuran (100 mL), water (10 mL) and oxalic acid (1.0 g, 0.022 mol) was heated at reflux for 40 hours. Workup provided 4-methoxy-4-methylpentanal (2.0 g). was heated at reflux for 40 hours
Source ID: ord-9040ef476b0b47f4b197c303f09b685aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1,1,4-trimethoxy-4-methylpentane (3.2 g, 0.018 mol), tetrahydrofuran (100 mL), water (10 mL) and oxalic acid (1.0 g, 0.022 mol) was heated at reflux for 40 hours. Workup provided 4-methoxy-4-methylpentanal (2.0 g). was heated at reflux for 40 hours
Source ID: ord-9040ef476b0b47f4b197c303f09b685aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred, cooled (-65~C) mixture of 2,6-dimethyl-2-methoxyhept-5-ene (125 g, 1.25 mol), methylene chloride (500 mL) and methanol (500 mL) was treated with a gas stream enriched with ozone. Upon the appearance of a blue color pure oxygen was passed through the mixture followed by nitrogen. Dimethyl sulfide (88 mL, 1.4 mol) was added and the mixture was allowed to stand 16 hours at 25~C. Upon workup 4-methoxy-4-methylpentanal was obtained, bp30 85-87~C (64.4 g); NMR(CDC13) 1.2(s,6H), 1.9(t,2H), 2.5(m,2H), 3.2(s,3H), 9.8(t,1H); IR(neat) 2975, 2825, 2725, 1730, 1470, 1370, 1090 cm-1 ; MS(m/e) 43, 73, 83, 115. A stirred, cooled was treated with a gas stream
Source ID: ord-c21013bc412f464086f14f8243deec77Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 4-methoxy-4-methylpentanal (60 g, 0.46 mol) and ethyl acetoacetate (156 g 1.2 mol) at 5~C. was added a 21% solution of piperidine in ethanol (4.1 mL). Further additions (4×18 mL) of the piperidine solution were made at about 24 hour intervals. The mixture was heated at reflux for 7 hours and concentrated to about 200 mL volume. Methanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added and the resulting mixture was heated at reflux 16 hours. Workup gave 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-one bp0.1 135-140~C. (69.2 g); NMR (CDCl3)δ1.2(s,6H), 0.9-1.6(m,5H), 1.9(s,3H), 5.9(brs,1H); IR(neat) 2975, 2930, 1675, 1640, 1380, 1080 cm-1 ; MS(m/e) 43, 73, 81, 109, 122, 163, 196. The mixture was heated at reflux for 7 hours concentrated to about 200 mL volume Methanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added the resulting mixture was heated at reflux 16 hours
Source ID: ord-06bec18194c34f19abd8d6df683eba83Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1,1,4-trimethoxy-4-methylpentane (3.2 g, 0.018 mol), tetrahydrofuran (100 mL), water (10 mL) and oxalic acid (1.0 g, 0.022 mol) was heated at reflux for 40 hours. Workup provided 4-methoxy-4-methylpentanal (2.0 g). was heated at reflux for 40 hours
Source ID: ord-ed0bfbe637004ed2bb9ba4aa468700feConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1,1,4-trimethoxy-4-methylpentane (3.2 g, 0.018 mol), tetrahydrofuran (100 mL), water (10 mL) and oxalic acid (1.0 g, 0.022 mol) was heated at reflux for 40 hours. Workup provided 4-methoxy-4-methylpentanal (2.0 g). was heated at reflux for 40 hours
Source ID: ord-ed0bfbe637004ed2bb9ba4aa468700feConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred, cooled (-65~C.) mixture of 2,6-dimethyl-2-methoxyhept-5-ene (125 g, 1.25 mol), methylene chloride (500 mL) and methanol (500 mL) was treated with a gas stream enriched with ozone. Upon the appearance of a blue color pure oxygen was passed through the mixture followed by nitrogen. Dimethyl sulfide (88 mL, 1.4 mol) was added and the mixture was allowed to stand 16 hours at 25~C. Upon workup 4-methoxy-4-methylpentanal was obtained, bp30 85-87~C. (64.4 g); NMR(CDCl3) 1.2(s,6H), 1.9(t,2H), 2.5(m,2H), 3.2(s,3H), 9.8(t,1H); IR(neat) 2975, 2825, 2725, 1730, 1470, 1370, 1090 cm-1 ; MS(m/e) 43, 73, 83, 115. A stirred, cooled was treated with a gas stream
Source ID: ord-a310b8b6d0604cf08b99fcc27f281161PubChem References
These sources are listed in the compound's public database record.
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