(1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol

Base Information

• Chemical Name: (1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol
• CAS No.: 222022-94-8
• Molecular Formula: C₂₂H₂₈O₂
• Molecular Weight: 324.463
• Mol file: 222022-94-8.mol

Synonyms:(1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol

Chemical Property of (1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol

There total 17 articles about (1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol 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: 90.0%

benzyl bromide (100-39-0) + (S)-5-methyl-3-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol (86996-95-4) → (1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol (222022-94-8)

Guidance literature:

With potassium carbonate; In acetone; Ambient temperature;

DOI:10.1016/S0040-4039(98)02487-3

Reference yield:

4-hydroxy-3-iodo-5-methoxybenzyl alcohol (37987-21-6) → (1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol (222022-94-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: (CBrCl₂)2; PPh₃ / CH₂Cl₂ / 0 - 20 °C

2.1: 3.60 g / LiAlH₄ / CH₂Cl₂; diethyl ether / 2.5 h / 20 °C

3.1: 79 percent / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 24.5 h / 20 °C

4.1: PPh₃; NaOAc / Pd(OAc)2 / dimethylformamide / 120 °C

4.2: 72 percent / H₂ / Pd/C / ethanol / 12 h / atmospheric pressure

5.1: BH₃*THF; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza...

6.1: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

7.1: 98 percent / K₂CO₃ / acetone / 48 h

8.1: (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -60 °C

8.2: 98 percent / Et₃N / CH₂Cl₂ / 2 h / -60 - 20 °C

9.1: NH₂NH₂*H₂O / bis-(2-hydroxy-ethyl) ether / 4 h / 160 °C

9.2: 91 percent / NaOH / bis-(2-hydroxy-ethyl) ether / 6 h / 180 °C

10.1: 90 percent / BBr₃ / CH₂Cl₂ / 3 h / 0 °C

11.1: 78 percent / K₂CO₃ / acetone / 48 h

With dmap; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; 1,2-dibromo-1,1,2,2-tetrachloroethane; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza..; sodium acetate; boron tribromide; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; diethylene glycol; 4.1: Heck reaction / 5.1: Corey-Bakshi-Shibata reduction / 8.1: Swern oxidation / 8.2: Swern oxidation / 9.1: Wolff-Kishner reduction / 9.2: Wolff-Kishner reduction;

DOI:10.1021/ja001455r

Reference yield:

5-iodovaniline (5438-36-8) → (1'S)-2-benzyloxy-4-methyl-6-(1',2',2'-trimethylcyclopentyl)phenol (222022-94-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaBH₄; NaOH / methanol / 0 - 20 °C

2.1: (CBrCl₂)2; PPh₃ / CH₂Cl₂ / 0 - 20 °C

3.1: 3.60 g / LiAlH₄ / CH₂Cl₂; diethyl ether / 2.5 h / 20 °C

4.1: 79 percent / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 24.5 h / 20 °C

5.1: PPh₃; NaOAc / Pd(OAc)2 / dimethylformamide / 120 °C

5.2: 72 percent / H₂ / Pd/C / ethanol / 12 h / atmospheric pressure

6.1: BH₃*THF; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza...

7.1: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

8.1: 98 percent / K₂CO₃ / acetone / 48 h

9.1: (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -60 °C

9.2: 98 percent / Et₃N / CH₂Cl₂ / 2 h / -60 - 20 °C

10.1: NH₂NH₂*H₂O / bis-(2-hydroxy-ethyl) ether / 4 h / 160 °C

10.2: 91 percent / NaOH / bis-(2-hydroxy-ethyl) ether / 6 h / 180 °C

11.1: 90 percent / BBr₃ / CH₂Cl₂ / 3 h / 0 °C

12.1: 78 percent / K₂CO₃ / acetone / 48 h

With dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; 1,2-dibromo-1,1,2,2-tetrachloroethane; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza..; sodium acetate; boron tribromide; potassium carbonate; hydrazine hydrate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; diethylene glycol; 5.1: Heck reaction / 6.1: Corey-Bakshi-Shibata reduction / 9.1: Swern oxidation / 9.2: Swern oxidation / 10.1: Wolff-Kishner reduction / 10.2: Wolff-Kishner reduction;

DOI:10.1021/ja001455r

upstream raw materials:

benzyl bromide

(S)-5-methyl-3-(1,2,2-trimethylcyclopentyl)benzene-1,2-diol

(1R,2R)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentyl-1-carbaldehyde

(1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol

Downstream raw materials:

1-Benzyloxy-2-isopropoxy-5-methyl-3-((S)-1,2,2-trimethyl-cyclopentyl)-benzene

3,3'-Dimethoxy-6,6'-dimethyl-4,4'-bis-((S)-1,2,2-trimethyl-cyclopentyl)-biphenyl-2,2'-diol

2-Ethoxy-5-methyl-3-((S)-1,2,2-trimethyl-cyclopentyl)-phenol

(1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-5-(1'',2'',2''-trimethylcyclopentyl)-3,4-(diphenylmethylidenedioxy)benzoate