Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester

Base Information

• Chemical Name: Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester
• CAS No.: 108376-60-9
• Molecular Formula: C₂₅H₃₂O₃
• Molecular Weight: 380.527

Synonyms:Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester

Chemical Property of Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester

Chemical Property:

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Technology Process of Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester

There total 14 articles about Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester 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: 95.0%

Benzoesaeure-<4-<(1'R)-3'-(3-hydroxy-1-butenyl)-2',2',4'-trimethyl-3'-cyclohexenyl>-2-methyl-2-butenyl>-ester → Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester (108376-60-9)

Guidance literature:

With manganese(IV) oxide; In diethyl ether; for 15h; Ambient temperature;

DOI:10.1002/hlca.19860690315

Reference yield:

(R)-2,2,4-trimethyl-3-cyclohexen-1-acetaldehyde (108361-18-8) → Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester (108376-60-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 95 percent / PPTS / benzene / 23 h / Heating

2: 1.) Me₂S*BH₃, 3.) 30percent H₂O₂, 3N NaOH / 1.) ether, 0 deg C, 15 min, 2.) RT, 4 h, 3.) reflux, 1 h

3: 82 percent / CrO₃, pyridine / CH₂Cl₂ / 0.25 h

4: 99 percent / H₂O / PPTS / acetone / 48 h / Heating

5: 78 percent / NaOEt / CH₂Cl₂; ethanol / 0.5 h / 0 °C

6: TsOH*H₂O / benzene / 45 h / Heating

7: LiAlH₄ / diethyl ether / 1 °C / Heating

8: 84 percent / H₂O / TsOH*H₂O / acetone / 42 h / Heating

9: TFA / 23 h / Ambient temperature

10: BuLi / tetrahydrofuran; hexane / 0.5 h / Ambient temperature

11: 2.) 2N HCl / 1.) THF, -10 deg C, 2.) acetone, H₂O, 3 h

12: PPTS / dimethylformamide / 2 h / 80 °C

13: 95 percent / LiAlH₄ / tetrahydrofuran / 18 h / Heating

14: 72 percent / pyridine / 65 h / 4 °C

15: 95 percent / MnO₂ / diethyl ether / 15 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; water; dihydrogen peroxide; sodium ethanolate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1002/hlca.19860690315

Reference yield:

(R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile (108361-17-7) → Benzoesaeure-<4-<(1'R)-2',2',4-trimethyl-3'-(3-oxo-1-butenyl)-3'-cyclohexenyl>-2-methyl-3-butenyl>ester (108376-60-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 93 percent / DIBAH / hexane / 1.) -60 deg C, 2.) RT, 1 h

2: 95 percent / PPTS / benzene / 23 h / Heating

3: 1.) Me₂S*BH₃, 3.) 30percent H₂O₂, 3N NaOH / 1.) ether, 0 deg C, 15 min, 2.) RT, 4 h, 3.) reflux, 1 h

4: 82 percent / CrO₃, pyridine / CH₂Cl₂ / 0.25 h

5: 99 percent / H₂O / PPTS / acetone / 48 h / Heating

6: 78 percent / NaOEt / CH₂Cl₂; ethanol / 0.5 h / 0 °C

7: TsOH*H₂O / benzene / 45 h / Heating

8: LiAlH₄ / diethyl ether / 1 °C / Heating

9: 84 percent / H₂O / TsOH*H₂O / acetone / 42 h / Heating

10: TFA / 23 h / Ambient temperature

11: BuLi / tetrahydrofuran; hexane / 0.5 h / Ambient temperature

12: 2.) 2N HCl / 1.) THF, -10 deg C, 2.) acetone, H₂O, 3 h

13: PPTS / dimethylformamide / 2 h / 80 °C

14: 95 percent / LiAlH₄ / tetrahydrofuran / 18 h / Heating

15: 72 percent / pyridine / 65 h / 4 °C

16: 95 percent / MnO₂ / diethyl ether / 15 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; water; dihydrogen peroxide; sodium ethanolate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1002/hlca.19860690315

upstream raw materials:

(R)-2,2,4-trimethyl-3-cyclohexen-1-acetaldehyde

(R)-2,2,4-trimethyl-3-cyclohexen-1-acetonitrile

(3R)-3-oxo-2,2,4-trimethylcyclohexan-1-acetaldehyde

(3R)-3-(4'-hydroxy-3'-methyl-2'-butenyl)-2,2,6-trimethylcyclohexanone

Downstream raw materials:

4-<(5'R)-5'-(4-hydroxy-3-methyl-2-butenyl)-2',6',6'-trimethyl-1'-cyclohexenyl>-3-buten-2-onE

(all-E,2R,2'R)-2,2'-bis(4-hydroxy-3-methyl-2-butenyl)-β,β-carotin

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