endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate

Base Information

• Chemical Name: endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate
• CAS No.: 114273-39-1
• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.3
• Mol file: 114273-39-1.mol

Synonyms:endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate

Chemical Property of endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate

There total 11 articles about endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate 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: 60.0%

2-(hydroxymethyl)-cis-bicyclo<3.3.0>octa-2,7-dien-exo-4-yl 4-hydroxybenzoate (114273-38-0) → endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate (114273-39-1)

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In dichloromethane; acetone; for 22h; Ambient temperature;

Reference yield:

4-acetyloxy-benzoic acid (2345-34-8) → endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate (114273-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-(dimethylamino)pyridine, p-toluenesulfonic acid monohydrate, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 24 h / Ambient temperature

2: 77 percent / sodium borohydride / ethanol / -78 deg C, 0.5 h, room temp. 1 h

3: 60 percent / t-BuOOH / VO(acac)2 / CH₂Cl₂; acetone / 22 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; bis(acetylacetonate)oxovanadium; In ethanol; dichloromethane; acetone;

Reference yield:

cis-bicyclo<3.3.0>octa-2,7-diene (41164-14-1) → endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate (114273-39-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 81 percent / SnCl₄ / CH₂Cl₂ / 19 h / -78 - -30 °C

2: 86 percent / LiAlH₄ / tetrahydrofuran / 19 h / reflux, then room temp.

3: NaIO₄ / acetone; H₂O / 19 h / Ambient temperature

4: sodium borohydride / ethanol / -78 deg C, 1 h, room temp. 22 h

5: 81 percent / t-BuOOH / VO(acac)2 / benzene / 24 h / Ambient temperature

6: DMSO, oxalylchloride / CH₂Cl₂ / 0.42 h / -78 °C

7: triethylamine / CH₂Cl₂ / 17 h / -78 deg C to room temp.

8: 4-(dimethylamino)pyridine, p-toluenesulfonic acid monohydrate, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 24 h / Ambient temperature

9: 77 percent / sodium borohydride / ethanol / -78 deg C, 0.5 h, room temp. 1 h

10: 60 percent / t-BuOOH / VO(acac)2 / CH₂Cl₂; acetone / 22 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; Chloro-oxo-acetic acid; tin(IV) chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; benzene;

upstream raw materials:

2-(hydroxymethyl)-cis-bicyclo<3.3.0>octa-2,7-dien-exo-4-yl 4-hydroxybenzoate

4-acetyloxy-benzoic acid

cis-bicyclo<3.3.0>octa-2,7-diene

(1S,3aS,6aS)-1,3a,4,6a-Tetrahydro-pentalene-1-carbaldehyde

Downstream raw materials:

(-)-specionin