(rac)-trans-caronaldehyde methyl ester dimethyl acetal

Base Information

• Chemical Name: (rac)-trans-caronaldehyde methyl ester dimethyl acetal
• CAS No.: 62250-31-1
• Molecular Formula: C₁₀H₁₈O₄
• Molecular Weight: 202.251
• Mol file: 62250-31-1.mol

Synonyms:

Chemical Property of (rac)-trans-caronaldehyde methyl ester dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (rac)-trans-caronaldehyde methyl ester dimethyl acetal

There total 15 articles about (rac)-trans-caronaldehyde methyl ester dimethyl acetal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.7%

methanol (67-56-1) + (rac)-trans-methyl 3-(α-methoxy-α-phenylthio)methyl-2,2-dimethylcyclopropanecarboxylate → (rac)-trans-caronaldehyde methyl ester dimethyl acetal (26770-98-9,54142-67-5,59829-77-5,62250-31-1,79813-17-5,105500-53-6,105817-13-8,124510-09-4,132015-00-0)

Guidance literature:

With iodine; for 24h; Ambient temperature;

Reference yield:

5-iodomethyl-4,4-dimethyltetrahydrofuran-2-one (65371-41-7) → (rac)-trans-caronaldehyde methyl ester dimethyl acetal (26770-98-9,54142-67-5,59829-77-5,62250-31-1,79813-17-5,105500-53-6,105817-13-8,124510-09-4,132015-00-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 79.1 percent / potassium carbonate / 1.5 h / Ambient temperature

2: 20.4 percent / LiN(SiMe₃)2 / tetrahydrofuran; hexane / 4 h / -30 °C

3: 1.) sodium hydride / 1.) THF, RT, 20 min, 2.) THF, reflux, 5h

4: 100 percent / 30percent aq. hydrogen peroxide / methanol / 120 h / Ambient temperature

5: 44.5 percent / trifluoroacetic anhydride, 2,6-lutidine / acetonitrile / 4 h / -25 °C

6: 91 percent / iodine / 15 h / Ambient temperature

7: 32.3 percent / 10percent aq. hydrochloric acid / tetrahydrofuran / 55 h / Ambient temperature

8: 1.) 2,6-lutidine, trifluoroacetic anhydride; 2.) potassium carbonate / 1.) acetonitrile, -30 deg C, 2h; 2.) acetonitrile, RT, 1 h

9: 76.7 percent / iodine / 24 h / Ambient temperature

With 2,6-dimethylpyridine; hydrogenchloride; dihydrogen peroxide; iodine; sodium hydride; potassium carbonate; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; acetonitrile;

Reference yield:

3,3-dimethylpent-4-enoic acid (7796-73-8) → (rac)-trans-caronaldehyde methyl ester dimethyl acetal (26770-98-9,54142-67-5,59829-77-5,62250-31-1,79813-17-5,105500-53-6,105817-13-8,124510-09-4,132015-00-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 96.1 percent / aq. NaHCO₃, I₂, KI / 1 h / Ambient temperature

2: 79.1 percent / potassium carbonate / 1.5 h / Ambient temperature

3: 20.4 percent / LiN(SiMe₃)2 / tetrahydrofuran; hexane / 4 h / -30 °C

4: 1.) sodium hydride / 1.) THF, RT, 20 min, 2.) THF, reflux, 5h

5: 100 percent / 30percent aq. hydrogen peroxide / methanol / 120 h / Ambient temperature

6: 44.5 percent / trifluoroacetic anhydride, 2,6-lutidine / acetonitrile / 4 h / -25 °C

7: 91 percent / iodine / 15 h / Ambient temperature

8: 32.3 percent / 10percent aq. hydrochloric acid / tetrahydrofuran / 55 h / Ambient temperature

9: 1.) 2,6-lutidine, trifluoroacetic anhydride; 2.) potassium carbonate / 1.) acetonitrile, -30 deg C, 2h; 2.) acetonitrile, RT, 1 h

10: 76.7 percent / iodine / 24 h / Ambient temperature

With 2,6-dimethylpyridine; hydrogenchloride; dihydrogen peroxide; iodine; sodium hydride; sodium hydrogencarbonate; potassium carbonate; trifluoroacetic anhydride; potassium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; acetonitrile;

upstream raw materials:

triphenylphosphonio-1-methylethanide

monofumaraldehyde dimethylacetal monomethylester

methanol

5-iodomethyl-4,4-dimethyltetrahydrofuran-2-one