trans-1,2-dihydroxy-1,2-dihydro-4-chlorobenzene

Base Information

• Chemical Name: trans-1,2-dihydroxy-1,2-dihydro-4-chlorobenzene
• CAS No.: 98575-78-1
• Molecular Formula: C₆H₇ClO₂
• Molecular Weight: 146.573
• Mol file: 98575-78-1.mol

Synonyms:

Chemical Property of trans-1,2-dihydroxy-1,2-dihydro-4-chlorobenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-1,2-dihydroxy-1,2-dihydro-4-chlorobenzene

There total 7 articles about trans-1,2-dihydroxy-1,2-dihydro-4-chlorobenzene 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: 89.0%

(5α,6β)-2-chloro-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene (121073-21-0) → trans-1,2-dihydroxy-1,2-dihydro-4-chlorobenzene (26944-56-9,98575-78-1,121153-50-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo00273a005

Reference yield:

1-chloro-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,4-diene (121073-15-2) → trans-1,2-dihydroxy-1,2-dihydro-4-chlorobenzene (26944-56-9,98575-78-1,121153-50-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 39 percent / sodium phosphate, m-CPBA / CHCl₃ / 43 h / Ambient temperature

2: 80 percent / NaBH₄ / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h

3: 80 percent / sodium phosphate, tetrabutylammonium periodate / CHCl₃ / 14 h / Ambient temperature

4: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; tetrabutylammonium periodite; 3-chloro-benzenecarboperoxoic acid; sodium phosphate; In tetrahydrofuran; methanol; chloroform;

DOI:10.1021/jo00273a005

Reference yield:

3-chloro-6-(phenylseleno)cyclohex-2-en-1-one (121073-09-4) → trans-1,2-dihydroxy-1,2-dihydro-4-chlorobenzene (26944-56-9,98575-78-1,121153-50-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / NaBH₄, CeCl₃*7H₂O / ethanol / 1.5 h / 0 - 20 °C

2: Et₃N, DMAP / CH₂Cl₂ / 50 h / Heating

3: sodium phosphate, tetrabutylammonium periodate / CHCl₃ / 24 h

4: 39 percent / sodium phosphate, m-CPBA / CHCl₃ / 43 h / Ambient temperature

5: 80 percent / NaBH₄ / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h

6: 80 percent / sodium phosphate, tetrabutylammonium periodate / CHCl₃ / 14 h / Ambient temperature

7: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; tetrabutylammonium periodite; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium phosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform;

DOI:10.1021/jo00273a005

upstream raw materials:

(5α,6β)-2-chloro-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene

1-chloro-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,4-diene

3-chloro-6-(phenylseleno)cyclohex-2-en-1-one

(3β,4β)-1-chloro-3-hydroxy-4-(phenylseleno)cyclohex-1-ene

Downstream raw materials:

4-chlorocyclohexa-3,5-diene-1,2-dione