1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene

Base Information

• Chemical Name: 1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene
• CAS No.: 110174-07-7
• Molecular Formula: C₂₁H₂₄O₄
• Molecular Weight: 340.419

Synonyms:1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene

Chemical Property of 1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene

There total 12 articles about 1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene 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: 97.2%

1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2-dihydronaphthalene (110174-06-6) → 1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene (110174-07-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 4h; under 2068.6 Torr; Ambient temperature;

DOI:10.1021/jo00229a028

Reference yield:

1-iodo-5-methoxynaphthalene (61735-51-1) → 1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene (110174-07-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 8 min, 2.) THF, -78 deg C

2: oxalyl chloride / CH₂Cl₂ / 12 h / Ambient temperature

3: conc. ammonia / CHCl₃

4: 1.) triethyloxonium tetrafluoroborate / 1.) CH₂Cl₂, a) RT, 20 h, b) reflux, 5 h, 2.) CH₂Cl₂, reflux, 24 h

5: 2.) a) CF₃COOH, b) H₂O / 1.) THF, Et₂O, -60 deg C, 72 h, 2.) a) -78 deg C, 1 h

6: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

7: 89.9 percent / KOH, benzyltriethylammonium chloride / CH₂Cl₂ / 20 h / Ambient temperature

8: 81.2 percent / O₂, PdCl₂(MeCN)2, CuCl / methanol / 20 h / 45 °C

9: 1.) sodium hexamethyldisilazane, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 40 min

10: 97.2 percent / H₂ / 10percent Pd/C / methanol / 4 h / 2068.6 Torr / Ambient temperature

With dichloro bis(acetonitrile) palladium(II); potassium hydroxide; ammonium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; N-benzyl-N,N,N-triethylammonium chloride; water; hydrogen; oxygen; triethyloxonium fluoroborate; sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; trifluoroacetic acid; copper(l) chloride; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; chloroform;

DOI:10.1021/jo00229a028

Reference yield:

5-methoxy-1-naphthoic acid (51934-37-3) → 1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene (110174-07-7)

Guidance literature:

Multi-step reaction with 9 steps

1: oxalyl chloride / CH₂Cl₂ / 12 h / Ambient temperature

2: conc. ammonia / CHCl₃

3: 1.) triethyloxonium tetrafluoroborate / 1.) CH₂Cl₂, a) RT, 20 h, b) reflux, 5 h, 2.) CH₂Cl₂, reflux, 24 h

4: 2.) a) CF₃COOH, b) H₂O / 1.) THF, Et₂O, -60 deg C, 72 h, 2.) a) -78 deg C, 1 h

5: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

6: 89.9 percent / KOH, benzyltriethylammonium chloride / CH₂Cl₂ / 20 h / Ambient temperature

7: 81.2 percent / O₂, PdCl₂(MeCN)2, CuCl / methanol / 20 h / 45 °C

8: 1.) sodium hexamethyldisilazane, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 40 min

9: 97.2 percent / H₂ / 10percent Pd/C / methanol / 4 h / 2068.6 Torr / Ambient temperature

With dichloro bis(acetonitrile) palladium(II); potassium hydroxide; ammonium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; N-benzyl-N,N,N-triethylammonium chloride; water; hydrogen; oxygen; triethyloxonium fluoroborate; sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; trifluoroacetic acid; copper(l) chloride; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; chloroform;

DOI:10.1021/jo00229a028

upstream raw materials:

1-<(benzyloxy)methyl>-2-acetyl-2-hydroxy-5-methoxy-1,2-dihydronaphthalene

1-iodo-5-methoxynaphthalene

5-methoxy-1-naphthoic acid

5-methoxy-[1]naphthoyl chloride

Downstream raw materials:

(1R,2S)-1-Benzyloxymethyl-2-(1-hydroxy-ethyl)-5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ol

(1R,2R,4S)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester

(1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester

1-<(benzyloxy)methyl>-2-ethyl-2-hydroxy-5-methoxy-1,2,3,4-tetrahydronaphthalene

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