<(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon

Base Information

• Chemical Name: <(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon
• CAS No.: 65243-75-6
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.252
• Mol file: 65243-75-6.mol

Synonyms:<(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon

Chemical Property of <(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon

There total 65 articles about <(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon 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: 55.0%

trans-1-(4-benzyloxy-1,2,2-trimethylcyclopentyl)ethanone → trans-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)ethanone (65243-75-6,87859-78-7,87859-79-8,89195-48-2,111319-42-7,171868-58-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 1h;

DOI:10.1080/00397910008086973

Reference yield:

(R)-1,2,2-trimethyl-cyclopent-3-ene-1,3-dicarboxylic acid (87798-58-1) → <(1R,4S)-4-Hydroxy-1,2,2-trimethylcyclopentyl>methylketon (65243-75-6,171868-58-9)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium bromide, hydrobromic acid / 100 °C

2: 55 percent / aq. sodium carbonate / Heating

4: 95 percent / 2N-sodium hydroxide / 1.5 h / Heating

5: 1.) 0.5N-hydrochloric acid, hydrogen / 1.)platinum dioxide / 1.) glacial acetic acid, 20 deg C, 30 h, 2.) ether

6: 7 mg / 2N sodium hydroxide / 2 h / Heating

7: 55 percent / diethyl ether / 18 h / Heating

With hydrogenchloride; sodium hydroxide; hydrogen bromide; hydrogen; sodium carbonate; lithium bromide; platinum(IV) oxide; In diethyl ether;

Reference yield:

4-hydroxymethyl-4,5,5-trimethylcyclohex-2-en-1-one (87798-35-4) → cis-3-acetyl-3,4,4-trimethylcyclopentan-1-ol (65243-75-6,87859-78-7,87859-79-8,89195-48-2,111319-42-7,171868-58-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 11 g / hydrogen / 10percent palladised charcoal / ethanol

2: 9.0 g / 0.1N-sulphuric acid / methanol / 0.5 h / Heating

3: 4.5 g / CrO₃, aq. H₂SO₄ / acetone / 2 h / 20 °C

4: 4.0 g / N-potassium t-butoxide, oxygen / 2-methyl-propan-2-ol

5: 1.) 5percent aq. potassium hydroxide, 2.) orthophosphoric acid, sodium bismuthate / 1.) reflux, 2.) overnight

6: 450 mg / potassium borohydride, sodium hydroxide / H₂O / 16 h / 100 °C

7: 0.9 g / 10percent aq. sodium hydroxide

8: 0.6 g / diethyl ether / Heating

With chromium(VI) oxide; potassium hydroxide; sodium hydroxide; potassium borohydride; sodium bismuthate; phosphoric acid; N-potassium t-butoxide; sulfuric acid; hydrogen; oxygen; palladium on activated charcoal; In methanol; diethyl ether; ethanol; water; acetone; tert-butyl alcohol;

upstream raw materials:

(1R,4S)-4-Hydroxy-1,2,2-trimethycyclopentancarbonsaeure

methyllithium

2-Methyl-2-<(R)-1,2,2-trimethyl-3-cyclopenten-1-yl>-1,3-dioxolan

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Downstream raw materials:

(3S,5R)-8-hydroxy-3-trimethylsilyloxy-κ,χ-caroten-6-one

trikentriorhodin

3'-hydroxy-β,κ-caroten-6'-one

(2E,4E,6E,8E,10E,12E,14E,16E,18E)-1,20-Bis-((1S,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl)-4,8,13,17-tetramethyl-icosa-2,4,6,8,10,12,14,16,18-nonaene-1,20-dione

Refernces

• 1、 -. "Preparation of (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone and derivatives and stereoisomers of this compound". . . Retrieved 2008/06/13.
• 2、 Ruttimann,Engbert,Mayer,et al.. "Synthesis of optically active natural carotenoids and structurally related compounds. X. Synthesis of (3R,3'S,5'R)-capsanthin, 3S,5R,3'S,5'R)-capsorubin, (3'S,5'R)-cryptocapsin, and some related compounds. A new approach to optically active, five-membered-ring carotenoid building units by hydroboration". . p. 1939 - 1960. Retrieved 2007/10/02.