4-Hydroxy-benzoic acid (1aS,1bR,2R,4R,5aS,6R,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

Base Information

• Chemical Name: 4-Hydroxy-benzoic acid (1aS,1bR,2R,4R,5aS,6R,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester
• CAS No.: 109582-94-7
• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.422
• Mol file: 109582-94-7.mol

Synonyms:

Chemical Property of 4-Hydroxy-benzoic acid (1aS,1bR,2R,4R,5aS,6R,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Hydroxy-benzoic acid (1aS,1bR,2R,4R,5aS,6R,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

There total 120 articles about 4-Hydroxy-benzoic acid (1aS,1bR,2R,4R,5aS,6R,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl 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:

4-(benzyloxy)benzoic acid chloride (1486-50-6) → (+/-)-specionin (87946-74-5,96944-53-5,109582-94-7,109582-95-8,109582-96-9,109582-97-0,109582-98-1,109582-99-2,109583-00-8,113531-99-0,113532-00-6,113532-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) H₂, 2,) NaIO₄, 3.) PTSA / 1.) Pd/C

3: 50 percent / K₂CO₃ / methanol / 0.25 h

With dmap; sodium periodate; hydrogen; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1039/P19940000061

Reference yield:

4-(benzyloxy)benzoic acid chloride (1486-50-6) → (+/-)-2-epi,4-specionin (87946-74-5,96944-53-5,109582-94-7,109582-95-8,109582-96-9,109582-97-0,109582-98-1,109582-99-2,109583-00-8,113531-99-0,113532-00-6,113532-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) H₂, 2,) NaIO₄, 3.) PTSA / 1.) Pd/C

3: 3 mg / K₂CO₃ / methanol / 0.25 h

With dmap; sodium periodate; hydrogen; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1039/P19940000061

Reference yield:

(+/-)-exo,exo-6,7-bis(benzyloxy)-exo-4-(hydroxymethyl)-cis-bicyclo<3.3.0>oct-2-ene → (+/-)-specionin (87946-74-5,96944-53-5,109582-94-7,109582-95-8,109582-96-9,109582-97-0,109582-98-1,109582-99-2,109583-00-8,113531-99-0,113532-00-6,113532-01-7)

Guidance literature:

Multi-step reaction with 8 steps

1: NaHCO₃, MCPBA / CH₂Cl₂ / 3 h

2: 1.) (COCl)2, DMSO, ET₃N, 2.) DBU / 1.) CH₂Cl₂, -78 deg C, 10 min; -78 deg C -> room temperature, 2.) room temperature, 2 h

3: CeCl₃, NaBH₄ / methanol / 0.5 h / Ambient temperature

4: 42 percent / Et₃N / CH₂Cl₂ / 30 h / Ambient temperature

5: VO(acac)2, t-BuOOH / CH₂Cl₂ / 2 h / Heating

6: DMAP / CH₂Cl₂ / 2 h / Ambient temperature

7: 1.) H₂, 2,) NaIO₄, 3.) PTSA / 1.) Pd/C

8: 50 percent / K₂CO₃ / methanol / 0.25 h

With tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; oxalyl dichloride; bis(acetylacetonate)oxovanadium; hydrogen; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1039/P19940000061

upstream raw materials:

4-Benzyloxy-benzoic acid (1bR,5aS,6R)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

4-Benzyloxy-benzoic acid (1aS,1bS,2S,4S,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

4-(benzyloxy)benzoic acid chloride

(+/-)-(2-endo,3-exo)-bicyclo[2.2.1]hept-5-eno-2,3-dimethanol

Downstream raw materials:

(-)-specionin