(R)-4-methyl-6-(phenylmethoxy)hexane-1,4-diol

Base Information

• Chemical Name: (R)-4-methyl-6-(phenylmethoxy)hexane-1,4-diol
• CAS No.: 131700-32-8
• Molecular Formula: C₁₄H₂₂O₃
• Molecular Weight: 238.327
• Mol file: 131700-32-8.mol

Synonyms:

Chemical Property of (R)-4-methyl-6-(phenylmethoxy)hexane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-methyl-6-(phenylmethoxy)hexane-1,4-diol

There total 9 articles about (R)-4-methyl-6-(phenylmethoxy)hexane-1,4-diol 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:

2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethanol (64018-43-5) → (R)-4-methyl-6-(phenylmethoxy)hexane-1,4-diol (131700-32-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 2.) 24 h

2: 95 percent / 1 M aq. H₂SO₄ / tetrahydrofuran / 4 h / 40 °C

3: 98 percent / Et₃N / CH₂Cl₂ / 0.17 h / -10 °C

4: 97 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂ / 1 h / Ambient temperature

5: 96 percent / Li₂Cu₂Cl₄ / tetrahydrofuran / 1.) -78 deg C, 3 h, 2.) RT, overnight

6: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 30percent H₂O₂, 3 M aq. NaOH / 1.) THF, RT, 3 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 2Li⁽¹⁺⁾*Cl₄Cu₂^(2-); sulfuric acid; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0957-4166(00)86350-8

Reference yield:

(S)-citramalic acid (6236-09-5,2306-22-1) → (R)-4-methyl-6-(phenylmethoxy)hexane-1,4-diol (131700-32-8)

Guidance literature:

Multi-step reaction with 9 steps

2: 93 percent / lithium aluminium hydride / tetrahydrofuran / 18 h / Heating

3: 86 percent / p-toluenesulphonic acid / 20 h / Ambient temperature

4: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 2.) 24 h

5: 95 percent / 1 M aq. H₂SO₄ / tetrahydrofuran / 4 h / 40 °C

6: 98 percent / Et₃N / CH₂Cl₂ / 0.17 h / -10 °C

7: 97 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂ / 1 h / Ambient temperature

8: 96 percent / Li₂Cu₂Cl₄ / tetrahydrofuran / 1.) -78 deg C, 3 h, 2.) RT, overnight

9: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 30percent H₂O₂, 3 M aq. NaOH / 1.) THF, RT, 3 h

With sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; 2Li⁽¹⁺⁾*Cl₄Cu₂^(2-); sulfuric acid; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0957-4166(00)86350-8

Reference yield:

(R)-2-hydroxy-2-methyl-butan-1,4-dioic acid dimethyl ester (38574-61-7) → (R)-4-methyl-6-(phenylmethoxy)hexane-1,4-diol (131700-32-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / lithium aluminium hydride / tetrahydrofuran / 18 h / Heating

2: 86 percent / p-toluenesulphonic acid / 20 h / Ambient temperature

3: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 2.) 24 h

4: 95 percent / 1 M aq. H₂SO₄ / tetrahydrofuran / 4 h / 40 °C

5: 98 percent / Et₃N / CH₂Cl₂ / 0.17 h / -10 °C

6: 97 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH₂Cl₂ / 1 h / Ambient temperature

7: 96 percent / Li₂Cu₂Cl₄ / tetrahydrofuran / 1.) -78 deg C, 3 h, 2.) RT, overnight

8: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 30percent H₂O₂, 3 M aq. NaOH / 1.) THF, RT, 3 h

With sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; 2Li⁽¹⁺⁾*Cl₄Cu₂^(2-); sulfuric acid; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0957-4166(00)86350-8

upstream raw materials:

(R)-3-methyl-1-(phenylmethoxy)hex-5-en-3-ol

2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethanol

(S)-citramalic acid

(R)-2-hydroxy-2-methyl-butan-1,4-dioic acid dimethyl ester