(E)-3-((1R,5S)-5-Hydroxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid

Base Information

• Chemical Name: (E)-3-((1R,5S)-5-Hydroxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid
• CAS No.: 326907-26-0
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.3
• Mol file: 326907-26-0.mol

Synonyms:

Chemical Property of (E)-3-((1R,5S)-5-Hydroxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-((1R,5S)-5-Hydroxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid

There total 10 articles about (E)-3-((1R,5S)-5-Hydroxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid 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:

methyl (1S,2R,5S)-(9,9-dimethyl-8-methylene-3-oxabicyclo[3.3.1]non-6-en-2-yl)acetate (326907-28-2) → (E)-3-((1R,5S)-5-Hydroxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid (326907-26-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 37 percent / H₂ / PtO₂ / methanol / 27 °C

2: 100 percent / NaOH; MeOH

3: LDA / tetrahydrofuran

With methanol; sodium hydroxide; hydrogen; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol;

DOI:10.1016/S0957-4166(00)00345-1

Reference yield:

((1S,2R,5S)-6-Bromo-8-bromomethyl-9,9-dimethyl-3-oxa-bicyclo[3.3.1]non-7-en-2-yl)-acetic acid methyl ester (326907-27-1) → (E)-3-((1R,5S)-5-Hydroxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid (326907-26-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Zn / 1,2-dimethoxy-ethane / Heating

2: 37 percent / H₂ / PtO₂ / methanol / 27 °C

3: 100 percent / NaOH; MeOH

4: LDA / tetrahydrofuran

With methanol; sodium hydroxide; hydrogen; zinc; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane;

DOI:10.1016/S0957-4166(00)00345-1

Reference yield:

(2,2,4-trimethyl-3-cyclohexen-1-yl)methanol (55695-33-5) → (E)-3-((1R,5S)-5-Hydroxymethyl-2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid (326907-26-0)

Guidance literature:

Multi-step reaction with 6 steps

1: PPL (SIGMA type II) from Porcine pancreas / diisopropyl ether; hexane / 72 h / 20 °C

2: 57 percent / PPL (SIGMA type II) from Porcine pancreas / toluene / 48 h / 20 °C / pH 7

3: 100 percent / N-methylmorpholine / diethyl ether

4: 67 percent / methanesulfonic acid / diethyl ether

5: 100 percent / NaOH; MeOH

6: LDA / tetrahydrofuran

With 4-methyl-morpholine; methanol; sodium hydroxide; methanesulfonic acid; PPL (SIGMA type II) from Porcine pancreas; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; di-isopropyl ether; toluene;

DOI:10.1016/S0957-4166(00)00345-1

upstream raw materials:

((1R,2R,5S)-8,9,9-Trimethyl-3-oxa-bicyclo[3.3.1]non-7-en-2-yl)-acetic acid

(2,2,4-trimethyl-3-cyclohexen-1-yl)methanol

acetic acid-(2,2,4-trimethyl-cyclohex-3-enylmethyl ester)

(-)-(S)-2,2,4-trimethyl-3-cyclohexene-1-methanol

Downstream raw materials:

(E)-3-((1R,5S)-2,5,6,6-Tetramethyl-cyclohex-2-enyl)-acrylic acid

(E,2S,6R)-(-)-cis-α-irone