methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate

Base Information

• Chemical Name: methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate
• CAS No.: 236751-82-9
• Molecular Formula: C₂₅H₂₇ClO₉
• Molecular Weight: 506.937
• Mol file: 236751-82-9.mol

Synonyms:methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate

Chemical Property of methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate

There total 10 articles about methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate 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:

9-chloro-12-hydroxy-8,11-dimethoxy-1-methoxymethoxymethyl-3-methyl-6-oxo-6H-naphtho[2,3-c]chromene-4-carboxylic acid methyl ester (236751-78-3) → methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate (236751-82-9)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -40 ℃; for 3h;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1229::AID-ANIE1229>3.0.CO;2-B

Reference yield:

2-chloro-4-methoxyphenol (18113-03-6) → methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate (236751-82-9)

Guidance literature:

Multi-step reaction with 10 steps

1: Me₂AlCl / CH₂Cl₂ / 4.5 h / 0 °C

2: K₂CO₃ / acetone / 13 h / Heating

3: 90 percent / MnO₂ / CH₂Cl₂ / 17 h / 40 °C

4: NaH / tetrahydrofuran

5: H₂O; CF₃CO₂H / 1 h

6: NaOAc / 1 h / Heating

7: 87 percent / H₂O; NaOH / tetrahydrofuran; ethanol / 1 h / 70 °C

8: 78 percent / EDCI; DMAP / CH₂Cl₂ / 3 h

9: t-BuCO₂Na / Pd(OAc)2; PPh₃ / N,N-dimethyl-acetamide / 1.5 h / 110 °C

10: NaBH₄ / tetrahydrofuran; methanol / 3 h / -40 °C

With dmap; manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; water; sodium acetate; dimethylaluminum chloride; sodium hydride; sodium pivalate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium diacetate; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; acetone; 1: Alkylation / 2: Methylation / 3: Oxidation / 4: Wittig-Horner reaction / 5: Hydrolysis / 6: Cyclization / 7: Hydrolysis / 8: Esterification / 9: Cyclization / 10: Reduction;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1229::AID-ANIE1229>3.0.CO;2-B

Reference yield:

3-chloro-2,5-dimethoxybenzaldehyde (236751-58-9) → methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-(methoxymethoxy)methyl-6-methylbenzoate (236751-82-9)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / tetrahydrofuran

2: H₂O; CF₃CO₂H / 1 h

3: NaOAc / 1 h / Heating

4: 87 percent / H₂O; NaOH / tetrahydrofuran; ethanol / 1 h / 70 °C

5: 78 percent / EDCI; DMAP / CH₂Cl₂ / 3 h

6: t-BuCO₂Na / Pd(OAc)2; PPh₃ / N,N-dimethyl-acetamide / 1.5 h / 110 °C

7: NaBH₄ / tetrahydrofuran; methanol / 3 h / -40 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; water; sodium acetate; sodium hydride; sodium pivalate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium diacetate; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; 1: Wittig-Horner reaction / 2: Hydrolysis / 3: Cyclization / 4: Hydrolysis / 5: Esterification / 6: Cyclization / 7: Reduction;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1229::AID-ANIE1229>3.0.CO;2-B

upstream raw materials:

9-chloro-12-hydroxy-8,11-dimethoxy-1-methoxymethoxymethyl-3-methyl-6-oxo-6H-naphtho[2,3-c]chromene-4-carboxylic acid methyl ester

2-chloro-4-methoxyphenol

3-chloro-2,5-dimethoxybenzaldehyde

3-chloro-2,5-dimethoxybenzyl alcohol

Downstream raw materials:

methyl (+/-)-3-(6-chloro-1-hydroxy-3-hydroxymethyl-5,8-dimethoxynaphthalen-2-yl)-2-hydroxy-4-hydroxymethyl-6-methylbenzoate