Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester
CAS No.:160146-85-0
Molecular Formula:C₂₂H₂₈O₄
Molecular Weight:356.462
Hs Code.:

Synonyms:Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester

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Chemical Property of Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester

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Technology Process of Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester

There total 21 articles about Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl 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: 82.0%

: 98-88-4
benzoyl chloride

: 160146-82-7
[(1S,4R,7aR)-7a-Methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-methanol

: 160146-85-0
Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester

Guidance literature:: With pyridine;
DOI:10.1021/jo00099a002

Reference yield:

: 765-69-5
2-Methylcyclopentane-1,3-dione

: 160146-85-0
Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 88 percent / Pd(OAc)2/PPh₃ / tetrahydrofuran / 6 h / Ambient temperature

2: 95 percent / TMSOTf / 10 h / -2 - 0 °C

3: 1.) BH₃*Me₂S, 2.) H₂O₂, 3 N NaOH / 1.) THF, 0 deg C to r.t., 4 h, 2.) r.t. 14 h

4: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

5: NaI, NaHCO₃ / acetone / 2.5 h / Heating

6: 70 percent / NaH / dimethylformamide / 13 h / Ambient temperature

7: 95 percent / Amberlyst-15 / acetone / 14 h / Ambient temperature

8: 80 percent / t-BuOK / tetrahydrofuran / 0.5 h / -80 °C

9: 56 percent / diethyl ether / -80 °C

10: 95 percent / t-BuLi / tetrahydrofuran / 14 h

11: 93 percent / HCO₂H, Et₃N / Pd(acac)2/Bu₃P / benzene / 3 h / Ambient temperature

12: 61 percent / OsO₄ / dioxane; H₂O / 2 h / Ambient temperature

13: NaIO₄ / acetone / 3 h / Ambient temperature

14: 95 percent / TMSOTf / CH₂Cl₂ / 3 h / -25 °C

15: 56 percent / LDA, AcCl / 1.) THF, -50 deg C, 2.) MeOH, -80 deg C, 10 min

16: LiAlH₄ / diethyl ether

17: 82 percent / pyridine

With pyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; formic acid; dimethylsulfide borane complex; potassium tert-butylate; dihydrogen peroxide; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; triethylamine; acetyl chloride; sodium iodide; lithium diisopropyl amide; palladium diacetate; palladium(II) acetylacetonate; amberlyst-15; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00099a002

Reference yield:

: 70833-73-7
6-allyl-6-methyl-1,4,8,11-tetraoxadispiro[4.1.4.2]tridecane

: 160146-85-0
Benzoic acid (1S,4R,7aR)-7a-methyl-1-(2-methyl-[1,3]dioxolan-2-yl)-2,4,5,6,7,7a-hexahydro-1H-inden-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) BH₃*Me₂S, 2.) H₂O₂, 3 N NaOH / 1.) THF, 0 deg C to r.t., 4 h, 2.) r.t. 14 h

2: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

3: NaI, NaHCO₃ / acetone / 2.5 h / Heating

4: 70 percent / NaH / dimethylformamide / 13 h / Ambient temperature

5: 95 percent / Amberlyst-15 / acetone / 14 h / Ambient temperature

6: 80 percent / t-BuOK / tetrahydrofuran / 0.5 h / -80 °C

7: 56 percent / diethyl ether / -80 °C

8: 95 percent / t-BuLi / tetrahydrofuran / 14 h

9: 93 percent / HCO₂H, Et₃N / Pd(acac)2/Bu₃P / benzene / 3 h / Ambient temperature

10: 61 percent / OsO₄ / dioxane; H₂O / 2 h / Ambient temperature

11: NaIO₄ / acetone / 3 h / Ambient temperature

12: 95 percent / TMSOTf / CH₂Cl₂ / 3 h / -25 °C

13: 56 percent / LDA, AcCl / 1.) THF, -50 deg C, 2.) MeOH, -80 deg C, 10 min

14: LiAlH₄ / diethyl ether

15: 82 percent / pyridine

With pyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; formic acid; dimethylsulfide borane complex; potassium tert-butylate; dihydrogen peroxide; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; triethylamine; acetyl chloride; sodium iodide; lithium diisopropyl amide; palladium(II) acetylacetonate; amberlyst-15; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00099a002