methyl 2,4-dihydroxy-6-pentylbenzoate

Base Information

• Chemical Name: methyl 2,4-dihydroxy-6-pentylbenzoate
• CAS No.: 58016-28-7
• Molecular Formula: C13H18O4
• Molecular Weight: 238.284
• Hs Code.: 2918290090
• Mol file: 58016-28-7.mol

Synonyms:BEN570;Methyl olivetolate;methyl 2,6-dihydroxy-6-pentylbenzoate;methyl 6-n-pentyl-2,4-dihydroxybenzoate;methyl olivetocarboxylate;Benzoic acid,2,4-dihydroxy-6-pentyl-,methyl ester;2,4-Dihydroxy-6-pentyl-benzoesaeure-methylester;2,4-dihydroxy-6-pentyl-benzoic acid methyl ester;

Chemical Property of methyl 2,4-dihydroxy-6-pentylbenzoate

Chemical Property:

• Melting Point: 105-106 °C(Solv: benzene (71-43-2))
• Boiling Point: 409.3±30.0 °C(Predicted)
• PKA: 8.30±0.23(Predicted)
• PSA: 66.76000
• Density: 1.153±0.06 g/cm3(Predicted)
• LogP: 2.61710
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Dichloromethane; Ethyl Acetate

Purity/Quality:

99% ^*data from raw suppliers

Methylolivetolate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl Olivetolate is an intermediate in synthesizing Δ9-Tetrahydrocannabinolic Acid (Acid A & B) (T293235). It is one of the substances screened for in meconium drug testings for medicinal opiods among addicted mothers. Δ9-Tetrahydrocannabinolic Acid has been shown to protect dopaminergic neurons against 1-methyl-4-Ph pyridinium (MPP+) induced cell death.

Technology Process of methyl 2,4-dihydroxy-6-pentylbenzoate

There total 14 articles about methyl 2,4-dihydroxy-6-pentylbenzoate 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: 55.0%

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1) + (2-Pentyl-[1,3]dioxolan-2-yl)-acetyl chloride (83578-33-0) → methyl 2,6-dihydroxy-6-pentylbenzoate (58016-28-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)87498-5

Reference yield: 52.0%

1-(1-imidazolyl)-1-hexanone (60988-34-3) + 1,3,5-tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene (102342-54-1) → methyl 2,6-dihydroxy-6-pentylbenzoate (58016-28-7)

Guidance literature:

With titanium(IV) isopropylate; titanium tetrachloride; In dichloromethane; 1.) -78 deg C, 5 h, 2.) RT, overnight;

DOI:10.1021/jo00363a004

Reference yield: 36.0%

N,N-dimethylhexanamide (5830-30-8) + 3,5-dioxohexanoic acid methyl ester (29736-80-9) → methyl 2,6-dihydroxy-6-pentylbenzoate (58016-28-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -20 ℃; for 5h;

upstream raw materials:

diazomethane

2,4-dihydroxyl-6-pentylbenzoic acid

methanol

anziaic acid

Downstream raw materials:

methyl 4-benzyloxy-6-hydroxy-2-pentylbenzoate

methyl 2-hydroxy-4-isopropyloxy-6-pentylbenzoate

CBD

(+)-(3S,4S)-delta-1-tetrahydrocannabinol

Refernces

• 1、 -. "SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DEMETHYLATION STEP". Page/Page column 16-17. . Retrieved 2019/03/05.
• 2、 Chan, T. H.,Chaly, T.. "A BIOMIMETIC SYNTHESIS OF 1Δ-TETRAHYDROCANNABIOL". . p. 2935 - 2938. Retrieved 2007/10/02.