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Chemistry
Organic Building Blocks
Aryls
Methyl 2,4-dihydroxy-6-pentylbenzoate
Chemistry
Organic Building Blocks
Aryls
Fluorinated Building Blocks Esters Phenols Aliphatic Chain Hydrocarbons Benzene Compounds

[ CAS No. 58016-28-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 58016-28-7
Chemical Structure| 58016-28-7
Structure of 58016-28-7 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 58016-28-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 58016-28-7 ]

SDS Specification
Alternatived Products of [ 58016-28-7 ]

Product Details of [ 58016-28-7 ]

CAS No. :58016-28-7 MDL No. :MFCD06737776
Formula : C13H18O4 Boiling Point : -
Linear Structure Formula :- InChI Key :RQGAOBDPFOADCM-UHFFFAOYSA-N
M.W : 238.28 Pubchem ID :13939393
Synonyms :

Calculated chemistry of [ 58016-28-7 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 65.96
TPSA : 66.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 4.04
Log Po/w (WLOGP) : 2.62
Log Po/w (MLOGP) : 2.2
Log Po/w (SILICOS-IT) : 2.72
Consensus Log Po/w : 2.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.73
Solubility : 0.0446 mg/ml ; 0.000187 mol/l
Class : Soluble
Log S (Ali) : -5.15
Solubility : 0.0017 mg/ml ; 0.00000715 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.34
Solubility : 0.11 mg/ml ; 0.00046 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.28

Safety of [ 58016-28-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58016-28-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 58016-28-7 ]

[ 58016-28-7 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 186581-53-3 ]
  • [ 491-72-5 ]
  • [ 58016-28-7 ]
Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1937,vol. 57,p. 553,556
    Chemische Berichte,1937,vol. 70,p. 206,208
  • 2
  • [ 67-56-1 ]
  • [ 641-68-9 ]
  • [ 58016-28-7 ]
Reference： [1]Chemische Berichte,1935,vol. 68,p. 1705,1707
    Chemische Berichte,1937,vol. 70,p. 1826,1828
  • 3
  • [ 58016-28-7 ]
  • [ 52189-68-1 ]
Reference： [1]Chemische Berichte,1937,vol. 70,p. 1823,1825
[2]Chemische Berichte,1937,vol. 70,p. 1823,1825
  • 4
  • [ 60988-34-3 ]
  • [ 102342-54-1 ]
  • [ 58016-28-7 ]
Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 2423 - 2428
  • 5
  • [ 5830-30-8 ]
  • [ 29736-80-9 ]
  • [ 58016-28-7 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2272 - 2277
  • 6
  • [ 74590-73-1 ]
  • [ 83578-33-0 ]
  • [ 58016-28-7 ]
Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 2935 - 2938
  • 7
  • [ 22972-51-6 ]
  • [ 58016-28-7 ]
  • [ 16850-65-0 ]
Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 2935 - 2938
  • 8
  • [ 58016-28-7 ]
  • [ 100-39-0 ]
  • [ 94103-01-2 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
[2]Australian Journal of Chemistry,1987,vol. 40,p. 1451 - 1464
  • 9
  • [ 142-61-0 ]
  • [ 102342-54-1 ]
  • [ 58016-28-7 ]
Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 2423 - 2428
  • 10
  • [ 5830-30-8 ]
  • [ 616-38-6 ]
  • [ 123-54-6 ]
  • [ 58016-28-7 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2272 - 2277
  • 11
  • [ 58016-28-7 ]
  • [ 75-26-3 ]
  • [ 78135-63-4 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 12
  • [ 6175-23-1 ]
  • [ 108-59-8 ]
  • [ 58016-28-7 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2272 - 2277
  • 15
  • anziaic acid methyl ester [ No CAS ]
  • [ 58016-28-7 ]
Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1937,vol. 57,p. 134,139
    Chem.Abstr.,1939,p. 3371
  • 16
  • [ 58016-28-7 ]
  • [ 113487-78-8 ]
Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1451 - 1464
  • 17
  • [ 58016-28-7 ]
  • [ 103538-04-1 ]
Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1451 - 1464
  • 18
  • [ 58016-28-7 ]
  • [ 113487-85-7 ]
Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1451 - 1464
  • 19
  • [ 58016-28-7 ]
  • [ 113487-80-2 ]
Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1451 - 1464
  • 20
  • [ 58016-28-7 ]
  • [ 113500-97-3 ]
Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1451 - 1464
  • 21
  • [ 58016-28-7 ]
  • [ 113487-82-4 ]
Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1451 - 1464
  • 22
  • [ 58016-28-7 ]
  • [ 122849-76-7 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
[2]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 23
  • [ 58016-28-7 ]
  • [ 78135-68-9 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
[2]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 24
  • [ 58016-28-7 ]
  • [ 78135-69-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 25
  • [ 58016-28-7 ]
  • [ 78135-70-3 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 26
  • [ 58016-28-7 ]
  • [ 78150-52-4 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 27
  • [ 58016-28-7 ]
  • [ 78135-64-5 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 28
  • [ 58016-28-7 ]
  • [ 78135-66-7 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 29
  • [ 58016-28-7 ]
  • [ 78135-65-6 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 30
  • [ 58016-28-7 ]
  • methyl 3-<6-(2-acetoxyheptyl)-2,4-dihydroxybenzoyl>-4-hydroxy-6-methoxy-2-pentylbenzoate [ No CAS ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 31
  • [ 58016-28-7 ]
  • [ 78150-51-3 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 32
  • [ 58016-28-7 ]
  • [ 78150-50-2 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 855 - 869
  • 33
  • [ 58016-28-7 ]
  • [ 94103-03-4 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1621 - 1626
  • 34
  • [ 58016-28-7 ]
  • [ 94103-02-3 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1621 - 1626
[2]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 35
  • [ 58016-28-7 ]
  • [ 53530-21-5 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 36
  • [ 58016-28-7 ]
  • [ 122849-85-8 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 37
  • [ 58016-28-7 ]
  • [ 122849-86-9 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 38
  • [ 58016-28-7 ]
  • [ 122849-87-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 39
  • [ 58016-28-7 ]
  • [ 122849-88-1 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 40
  • [ 58016-28-7 ]
  • [ 122849-80-3 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 41
  • [ 58016-28-7 ]
  • [ 122849-78-9 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 42
  • [ 58016-28-7 ]
  • [ 101910-68-3 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 43
  • [ 58016-28-7 ]
  • [ 101910-78-5 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 44
  • [ 58016-28-7 ]
  • [ 122849-79-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 45
  • [ 58016-28-7 ]
  • [ 122849-91-6 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 46
  • [ 58016-28-7 ]
  • [ 122849-81-4 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 47
  • [ 58016-28-7 ]
  • [ 122849-89-2 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 48
  • [ 58016-28-7 ]
  • [ 122849-90-5 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 49
  • [ 58016-28-7 ]
  • [ 122849-83-6 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 50
  • [ 58016-28-7 ]
  • 3-(6-Benzyloxy-3-hydroxy-2-propionyl-1H-inden-4-yloxy)-4-hydroxy-6-methoxy-2-pentyl-benzoic acid methyl ester [ No CAS ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 51
  • [ 58016-28-7 ]
  • [ 122849-82-5 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 52
  • [ 58016-28-7 ]
  • [ 122849-84-7 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 53
  • [ 58016-28-7 ]
  • [ 122881-02-1 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 54
  • [ 58016-28-7 ]
  • [ 122849-92-7 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 55
  • [ 58016-28-7 ]
  • [ 122849-93-8 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 56
  • [ 58016-28-7 ]
  • [ 122849-77-8 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 57
  • [ 58016-28-7 ]
  • 4-Benzyloxy-3-[2,4-bis-benzyloxy-6-(3-oxo-pentyl)-benzoyl]-6-methoxy-2-pentyl-benzoic acid benzyl ester [ No CAS ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 441 - 448
  • 58
  • [ 529-47-5 ]
  • [ 58016-28-7 ]
Reference： [1]Chemische Berichte,1935,vol. 68,p. 634,636, 638
  • 59
  • [ 855875-40-0 ]
  • [ 58016-28-7 ]
Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1937,vol. 57,p. 553,556
    Chemische Berichte,1937,vol. 70,p. 206,208
  • 60
  • 2,4-bis-ethoxycarbonyloxy-6-pentyl-benzoic acid [ No CAS ]
  • [ 58016-28-7 ]
Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1937,vol. 57,p. 553,556
    Chemische Berichte,1937,vol. 70,p. 206,208
  • 61
  • [ 58016-28-7 ]
  • [ 861892-40-2 ]
  • methyl cannabidiolate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step 1: Condensation of p-mentha-2,8-dienol with methyl olivetolate (method ?a?):This step is identical whether followed by hydrolysis and decarboxylation by the pressure process or at ambient pressure, or whether a subsequent isomerization ?c? takes place before or after the hydrolysis ?b?.A 10 litre three-neck flask with stirrer, reflux condenser, internal thermometer and dropping funnel is initially charged with: 300 g (1.259 mol) of methyl olivetolate 196.4 g (1.290 mol) of p-mentha-2,8-dien-1-ol 2.5 litres of dichloromethane (preferably unstabilized, freshly distilled material) optionally, a water-binding agent, for example 100 g of anhydrous sodium sulphate or 120 g of magnesium sulphate, can be added. The mixture is stirred until a homogeneous solution has formed.The flask is immersed into an external ice-salt cooling bath and stirring is continued until an internal temperature of minus 15 C. has been attained.A solution of 59.5 g (0.419 mol) of boron trifluoride-diethyl etherate in 500 ml of unstabilized, dry dichloromethane is introduced into the dropping funnel.The boron trifluoride etherate solution is added dropwise with vigorous stirring and external cooling to the reaction mixture within approx. one hour, in the course of which an internal temperature of approx. minus 15 C. is maintained.The reaction solution becomes yellowish and turbid.Once the total amount of boron trifluoride etherate has been added, the mixture is stirred at minus 15 C. for another approx. 15 min.The flask is removed from the ice bath.Subsequently, a solution of 180 g (1.8 mol) of potassium hydrogencarbonate in 2 l of deionized water is allowed to run in with vigorous stirring within approx. 30 min, in the course of which evolution of carbon dioxide occurs towards the end.Stirring is continued for two more hours, then the mixture is transferred to a separating funnel and the aqueous phase (pH approx. 8) is removed and discarded.The organic phase is washed with two portions each of 1 l of deionized water.The organic phase is removed and concentrated on a rotary evaporator. Finally, the bath temperature is raised to 90 C. and the pressure is reduced to 3 mbar in order to remove residual solvent.Yield: 466 g (99%) of crude methyl cannabidiolate (CBDAMe), which contains approx. 10-20% unchanged starting material (methyl olivetolate).
Reference： [1]Patent: US2010/298579,2010,A1 .Location in patent: Page/Page column 12
  • 62
  • [ 58016-28-7 ]
  • [ 13956-29-1 ]
Reference： [1]Patent: US2010/298579,2010,A1
[2]Patent: US2015/336874,2015,A1
[3]Patent: CN106810426,2017,A
[4]Patent: CN106810426,2017,A
[5]Patent: CN106810426,2017,A
[6]Patent: CN106810426,2017,A
[7]Patent: WO2017/194173,2017,A1
  • 63
  • [ 58016-28-7 ]
  • [ 17766-02-8 ]
Reference： [1]Patent: US2010/298579,2010,A1
  • 64
  • [ 58016-28-7 ]
  • [ 861892-40-2 ]
  • [ 55658-71-4 ]
YieldReaction ConditionsOperation in experiment
70% Step 1: Coupling Step (in the Continuous Process); Synthesis of Cannabidiolic Acid Methyl Ester (I) (0206) 300 g (2.0 mole) menthadienol and 476 g (2.0 mole) olivetolic acid ester are dissolved at ca. 22 C. in 1,370 g of chlorobenzene (2,000 mL solution A), likewise 94 g (0.66 mole) boron trifluoride*etherate are dissolved in 640 g of chlorobenzene at ca. 22 C. (666 mL solution B)., Solution A at a flow rate of 72 mL/min and solution B at a flow rate of 24 mL/min are pumped into a stirred reaction chamber via two separate dosing pumps, from the reaction chamber the reaction composition runs via a PTFE hose into a stirred solution of 1,000 g of sodium bicarbonate. The total reaction time is ca. 20 min. After termination of the metering the hydrolyzed reaction solution is stirred for a further 30 min. (0207) Then the hydrolyzed reaction solution is transferred into a 5 L jacket reaction vessel, the aqueous phase is separated and the solvent chlorobenzene is removed in vacuo. Ca. 2,000 g of toluene are added to the remaining 730 g of raw material and the unreacted olivetolic acid ester is extracted through the addition of 1,200 g 1% aqueous sodium hydroxide solution (four times). After acidifying with semi conc. sulfuric acid and re-extraction of this aqueous phase, ca. 30% (140 g) of non converted olivetolic acid ester are recovered. (0208) There are ca. 520 g of cannabidiolic acid methyl ester (I) in the toluene phase, which corresponds to a theoretical yield of ca. 70%. This first intermediate serves as starting material for the following transesterification.
70% With boron trifluoride diethyl etherate; In chlorobenzene; at 20℃; for 1h; General procedure: A solution of (4R)-1 -methyl-4-(prop-1 -en-2-yl)cyclohex-2-en-i -ol (1 equiv) and <strong>[58016-28-7]methyl 2,4-dihydroxy-6-pentylbenzoate</strong> (1 equiv) or methyl 2,4-dihydroxy-6- propylbenzoate (1 equiv) in chlorobenzene (0.1 M) at room temperature was treated with BF3.OEt2 (0.15 equiv) in chlorobenzene (0.05 M). The solution was stirred for 1 hthen treated with aqueous NaHCO3 and extracted with DCM, dried (MgSO4) and concentrated. The residue was subjected to flash column chromatography (silica, 0 to 10% EtOAc/Hexane gradient elution) to give a colourless oil. Yields 60-70%
300 g (2.0 mol) menthadienol and 476 g (2.0 mol) olivetolic acid ester are dissolved at ca. 22 C in 1 ,370 g of chlorobenzene (2.000 rrsL solution A), likewise 94 g (0.66 mol) boron trifluoride*etherate are dissolved in 640 g of chlorobenzene at ca. 22 C (666 mL solution B)., Solution A at a flow rate of 72 mU min and solution B at a flow rate of 24 mL/ min are pumped into a stirred reaction chamber via two separate dosing pumps, from the reaction chamber the reaction composition runs via a PTFE hose into a stirred solution of 1 .000 g of sodium bicarbonate. The total reaction time is ca. 20 min. After termination of the metering the hydro- lyzed reaction solution is stirred for a further 30 min. Then the hydrolyzed reaction solution is transferred into a 5L jacket reaction vessel, the aqueous phase is separated and the solvent chlorobenzene is removed in vacuo. Ca. 2.000 g of toluene are added to the remaining 730 g of raw material and the un reacted olivetolic acid ester is extracted through the addition of 1 .200 g 1 % aqueous sodium hydroxide solution (four times). After acidifying with semi cone, sulfuric acid and re-extraction of this aqueous phase, ca. 30% (140 g) of non converted olivetolic acid ester are recovered. There are ca. 520 g of cannabidiolic acid methyl ester in the toluene phase, which corresponds to a theoretical yield of ca. 70%. This first intermediate serves as starting material for the following transesterifi cation.
With boron trifluoride diethyl etherate; In chlorobenzene; at 20℃; for 1h; A solution of (4R)-1 -methyl-4-(prop-1 -en-2-yl)cyclohex-2-en-1 -ol (1 equiv) and <strong>[58016-28-7]methyl 2,4-dihydroxy-6-pentylbenzoate</strong> (1 equiv) or methyl 2,4-dihydroxy-6- propylbenzoate (1 equiv) in chlorobenzene (0.1 M) at room temperature was treated with BF3.0Et2 (0.1 5 equiv) in chlorobenzene (0.05 M). The solution was stirred for 1 h then treated with aqueous NaHC03 and extracted with DCM, dried (MgS04) and concentrated. The residue was subjected to flash column chromatography (silica, 0 to 10% EtOAc/Hexane gradient elution) to give a colourless oil. Yields 60-70%

Reference： [1]Patent: US2015/336874,2015,A1 .Location in patent: Paragraph 0206-0208
[2]Patent: WO2019/33168,2019,A1 .Location in patent: Page/Page column 17; 18
[3]Patent: WO2017/194173,2017,A1 .Location in patent: Page/Page column 21
[4]Patent: WO2019/33164,2019,A1 .Location in patent: Page/Page column 17-18
  • 65
  • [ 58016-28-7 ]
  • 2-hydroxyethyl cannabidiolate [ No CAS ]
Reference： [1]Patent: US2015/336874,2015,A1
[2]Patent: WO2017/194173,2017,A1
  • 66
  • [ 58016-28-7 ]
  • [ 1972-08-3 ]
Reference： [1]Patent: US2015/336874,2015,A1
[2]Patent: WO2017/194173,2017,A1
  • 67
  • [ 13330-96-6 ]
  • [ 58016-28-7 ]
  • C18H29NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With potassium hydroxide; at 130℃; for 4h;Inert atmosphere; 119 g of methyl 2,4-dihydroxy-6-pentylbenzoate and 234 g of N, N-dimethylbutanolamine were charged into a500 mL three-necked flask and 33.6 g of potassium hydroxide was added with stirring, , And the reaction wasstirred at 130 C for 4 hours. The reaction solution was cooled to below 30 C, adjusted to pH 2 to 3 with 1N aqueous hydrochloric acid, extracted with n-heptane (250 mL x 2), adjusted to pH 10 with aqueous sodiumcarbonate, and n-heptane (250 mL x 2 ), Washed with water (150 mL) once, dried over anhydrous sodiumsulfate, concentrated to dryness under reduced pressure and then recrystallized from 4 g / m n-heptane. After drying, 134.1 g, yield 83% and HPLC purity 99.97%.
Reference： [1]Patent: CN106810426,2017,A .Location in patent: Paragraph 0047; 0048
  • 68
  • [ 1862-07-3 ]
  • [ 58016-28-7 ]
  • C20H33NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium hydroxide; at 130℃; for 4h;Inert atmosphere; 119 g of <strong>[58016-28-7]methyl 2,4-dihydroxy-6-pentylbenzoate</strong> and 145 g of N, N-dimethylhexanolamine were charged into a250 mL three-necked flask and 30.8 g of potassium hydroxide was added with stirring, , And the reaction wasstirred at 130 C for 4 hours. The reaction solution was cooled to below 30 C, adjusted to pH 2 to 3 with 1Naqueous hydrochloric acid, extracted with n-heptane (250 mL x 2), adjusted to pH 10 with aqueous sodiumcarbonate, and n-heptane (250 mL x 2 ), Washed with water (150 mL) once, dried over anhydrous sodiumsulfate, concentrated to dryness under reduced pressure, and then recrystallized from 4 g / m n-heptane. Afterdrying, 142.2 g, yield 81% and HPLC purity 99.75%.
Reference： [1]Patent: CN106810426,2017,A .Location in patent: Paragraph 0054; 0055
  • 69
  • [ 3238-75-3 ]
  • [ 58016-28-7 ]
  • C20H33NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium hydroxide; at 130℃; for 4h;Inert atmosphere; 119 g of <strong>[58016-28-7]methyl 2,4-dihydroxy-6-pentylbenzoate</strong> and 145.3 g of N, N-dipropylethanolamine were charged into a250 mL three-necked flask and 30.8 g of potassium hydroxide was added with stirring, The reaction was stirred at 130 C for 4 hours. The reaction solution was cooled to below 30 C, adjusted to pH 2 to 3 with 1N aqueous hydrochloric acid, extracted with n-heptane (250 mL x 2), adjusted to pH 10 with aqueous sodium carbonate,and n-heptane (250 mL x 2 ), Washed with water (150 mL) once, dried over anhydrous sodium sulfate,concentrated to dryness under reduced pressure, and then recrystallized from 4 g / m n-heptane. After drying,127.8 g was obtained, the yield was 81%, and the HPLC purity was 99.63%.
Reference： [1]Patent: CN106810426,2017,A .Location in patent: Paragraph 0061; 0062
  • 70
  • [ 58016-28-7 ]
  • C28H43NO4 [ No CAS ]
Reference： [1]Patent: CN106810426,2017,A
  • 71
  • [ 58016-28-7 ]
  • C30H47NO4 [ No CAS ]
Reference： [1]Patent: CN106810426,2017,A
  • 72
  • [ 58016-28-7 ]
  • C30H47NO4 [ No CAS ]
Reference： [1]Patent: CN106810426,2017,A
  • 73
  • [ 58016-28-7 ]
  • C26H39NO4 [ No CAS ]
Reference： [1]Patent: CN106810426,2017,A
  • 74
  • [ 108-01-0 ]
  • [ 58016-28-7 ]
  • C16H25NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium hydroxide; at 130℃; for 4h;Inert atmosphere; First, 119 g of <strong>[58016-28-7]methyl 2,4-dihydroxy-6-pentylbenzoate</strong> and 89 g of N, N-dimethylethanolamine were charged into a 250 mL three-necked flask and 30.8 g of potassium hydroxide was added with stirring, and the reaction was stirred at 130 C for 4 hours. The reaction solution was cooled to below 30 C, adjusted to pH 2 to 3 with1N aqueous hydrochloric acid, extracted with n-heptane (250 mL x 2), adjusted to pH 10 with aqueous sodium carbonate, and n-heptane (250 mL x 2 ), Washed with water (150 mL) once, dried over anhydrous sodium sulfate, concentrated to dryness under reduced pressure and then recrystallized from 4 g / m n-heptane. After drying, 103 g was obtained, the yield was 70% and the HPLC purity was 99.84%.
Reference： [1]Patent: CN106810426,2017,A .Location in patent: Paragraph 0040; 0041
  • 75
  • [ 106-24-1 ]
  • [ 58016-28-7 ]
  • [ 63953-93-5 ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate; In chloroform; at -20℃; for 0.25h; General procedure: A solution of geraniol (1 equiv) and <strong>[58016-28-7]methyl 2,4-dihydroxy-6-pentylbenzoate</strong> (3 equiv) or methyl 2,4-dihydroxy-6-propylbenzoate (3 equiv) in CHCI3 (0.1 M) at -20 C was treated with BF3.OEt2 (0.1 equiv) in CHCI3 (0.1 M) and stirred for 0.25 h. Water was added followed and extracted with DCM, dried (MgS04) and concentrated. The residue was subjected to flash column chromatography (silica, 0 to 5% EtOAc/Hexane gradient elution) to give a colourless oil. Yields 30-40%
With boron trifluoride diethyl etherate; In chloroform; at -20℃; for 0.25h; A solution of geraniol (1 equiv) and <strong>[58016-28-7]methyl 2,4-dihydroxy-6-pentylbenzoate</strong> (3 equiv) or methyl 2,4-dihydroxy-6-propylbenzoate (3 equiv) in CHCI3 (0.1 M) at -20 C was treated with BF3.OEt2 (0.1 equiv) in CHCI3 (0.1 M) and stirred for 0.25 h. Water was added followed and extracted with DCM, dried (MgS04) and concentrated. The residue was subjected to flash column chromatography (silica, 0 to 5% EtOAc/Hexane gradient elution) to give a colourless oil. Yields 30-40%.
Reference： [1]Patent: WO2019/33168,2019,A1 .Location in patent: Page/Page column 19
[2]Patent: WO2019/33164,2019,A1 .Location in patent: Page/Page column 19
  • 76
  • [ 58016-28-7 ]
  • [ 5392-40-5 ]
  • [ 63953-93-5 ]
YieldReaction ConditionsOperation in experiment
With calcium hydroxide; In methanol; at 140℃; for 1.5h;Sealed tube; R1 is propyl or pentyl. A solution of citral (3 equiv), 2,4-dihydroxy-6-pentylbenzoate (1 equiv) or methyl 2,4-dihydroxy-6-propylbenzoate (1 equiv) and Ca(OH)2 (1 equiv) in methanol (0.5 M) in a sealed tube was heated at 140 C for 1 .5 h. The cooled solution was diluted with EtOAc and 1 M HCI. The separated aqueous phase was extracted with EtOAc and the combined organic layers were dried (MgS04) and concentrated. The residue was subjected to flash column chromatography (silica, 30% DCM/Hexane elution) to give a colourless oil. Yields 75-85%.
Reference： [1]Patent: WO2019/33164,2019,A1 .Location in patent: Page/Page column 19-20
  • 77
  • [ 18402-83-0 ]
  • [ 108-59-8 ]
  • [ 58016-28-7 ]
YieldReaction ConditionsOperation in experiment
A solution of methanol (250 mL) at 0 C was treated with sodium (12.0 g, 0.52 mol) in portions and stirred until dissolved. Dimethyl malonate (67.7 mL, 0.59 mol) was then added followed by (E)-non-3-en-2-one (59 g, 0.42 mol) and the solution heated at reflux for 8 h. The methanol was removed then diluted with water (400 mL) and washed with CHCI3 (300 mL). The aqueous later was acidified and extracted with CHCI3 (3 x 250 mL). The combined organic layers were dried (MgS04) and concentrated to give a white solid. The white solid (8.17 g, 34.0 mmol) was dissolved in DMF (20 ml) and cooled to 0 C. A solution of Br2 (1 .75 mL, 34.0 mmol) in DMF (6.6 mL) was slowly added and the solution stirred at 20 C for 1 h. The solution was then heated to 80 C for 1 6 h before cooling and treatment with 5% Na2S203 aqueous solution (200 mL) and being extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried (MgS04) and concentrated. The crude material was recrystallized from DCM/hexane to give a white solid
(0075) A solution of methanol (250 mL) at 0 C was treated with sodium (12.0 g, 0.52 mol) in portions and stirred until dissolved. Dimethyl malonate (67.7 mL, 0.59 mol) was then added followed by (E)-non-3-en-2-one (59 g, 0.42 mol) and the solution heated at reflux for 8 h. The methanol was removed then diluted with water (400 mL) and washed with CHCI3 (300 mL). The aqueous later was acidified and extracted with CHCI3 (3 x 250 mL). The combined organic layers were dried (MgS04) and concentrated to give a white solid. (0076) The white solid (8.17 g, 34.0 mmol) was dissolved in DMF (20 ml) and cooled to 0 C. A solution of Br2 (1 .75 mL, 34.0 mmol) in DMF (6.6 mL) was slowly added and the solution stirred at 20 C for 1 h. The solution was then heated to 80 C for 1 6 h before cooling and treatment with 5% Na2S203 aqueous solution (200 mL) and being extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried (MgS04) and concentrated. The crude material was recrystallized from DCM/hexane to give a white solid.
Reference： [1]Patent: WO2019/33168,2019,A1 .Location in patent: Page/Page column 16
[2]Patent: WO2019/33164,2019,A1 .Location in patent: Page/Page column 16-17
  • 78
  • [ 58016-28-7 ]
  • [ 16850-65-0 ]
Reference： [1]Patent: WO2019/33164,2019,A1
  • 79
  • [ 58016-28-7 ]
  • [ 23978-85-0 ]
Reference： [1]Patent: WO2019/33164,2019,A1
  • 80
  • [ 58016-28-7 ]
  • [ 1244-58-2 ]
Reference： [1]Patent: WO2019/33164,2019,A1
  • 81
  • [ 58016-28-7 ]
  • [ 25555-57-1 ]
Reference： [1]Patent: WO2019/33164,2019,A1
  • 82
  • [ 58016-28-7 ]
  • C24H34O5 [ No CAS ]
Reference： [1]Patent: WO2020/1770,2020,A1
  • 83
  • [ 58016-28-7 ]
  • [ 74219-29-7 ]
Reference： [1]Patent: WO2020/1770,2020,A1
  • 84
  • [ 58016-28-7 ]
  • C27H40O5 [ No CAS ]
Reference： [1]Patent: WO2020/1770,2020,A1
  • 85
  • [ 58016-28-7 ]
  • (1R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-en-1-ol [ No CAS ]
  • C23H32O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate; In toluene; 71.4 g (300 mMol) <strong>[58016-28-7]olivetol methylester</strong> and 50 g (330 mMol) 1 R,4S-menthadienol were dissolved together with toluene to reach a combined volume of 400 ml -> Solution A. 21.3 g (150 mMol) BF3 etherate was dissolved with toluene to reach a volume of 300 ml -> Solution B. Both reaction solutions were then put through two separate pump systems and the continuous flow reactor (rotation: 1200 U/min, solution A: 24 ml/min, solution B: 12 ml/min). Solution B started before and ended after solution A to guarantee that catalyst is always present in the reaction chamber. The reaction mixture was continuously collected in a 2 liter lab reactor (30 C mantel temperature, 300 rpm) filled with 700 ml saturated NaHCCh solution. The aqueous solution was discarded; the organic solution was washed at 45 degrees 4 times with 250 ml_ of 1 % NaOH solution. After washing, the organic solu- tion was evaporated to dryness to give 94.58 g of raw (+)-CBD methylester (purity = 78 %, yield 68 %). The raw compound can be used further without purification. The crude product was purified by flash chromatography (eluent system cyclohexane / ethyl acetate = 40/1 v/v). GC purity: 99.1 %. Chiral GC analysis: enantiomeric excess 99 % (for enantiomeric pure starting material). 1 H NMR (400 MHz, CDCh) d 1 1.98 (s, 1 H), 6.50 (s, 1 H), 6.21 (s, 1 H), 5.55 (s, 1 H), 4.52 (p, J = 2.4, 1.4 Hz, 1 H), 4.41 - 4.36 (m, 1 H), 4.16 - 4.06 (m, 1 H), 3.90 (s, 3H), 2.89 - 2.79 (m, 1 H), 2.78 - 2.69 (m, 1 H), 2.44 - 2.33 (m, 1 H), 2.29 - 2.15 (m, 1 H), 2.09 (dq, J = 17.9, 4.0, 2.5 Hz, 1 H), 1.84 - 1.76 (m, 2H), 1.80 - 1.77 (m, 3H), 1.72 - 1.68 (m, 3H), 1.57 - 1.46 (m, 2H), 1.38 - 1.28 (m, 4H), 0.89 (t, J = 6.8 Hz, 3H). 13C NMR (101 MHz, CDCh) d 172.62, 163.1 1 , 159.91 , 147.23, 145.94, 140.19, 124.06, 1 14.38, 1 1 1.49, 1 1 1 .23, 103.91 , 51.73, 46.66, 36.83, 35.40, 32.10, 31 .14, 30.24, 27.84, 26.92, 23.71 , 22.55, 18.83, 14.10.
Reference： [1]Patent: WO2020/1770,2020,A1 .Location in patent: Page/Page column 20

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