500-49-2

Basic information

• Product Name: 5-Propyl-1,3-benzenediol
• Synonyms: 5-Propyl-1,3-benzenediol;Divarinol
• CAS NO: 500-49-2
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• Mol File: 500-49-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 82.8°C
• Boiling Point: 234.66°C (rough estimate)
• Flash Point: 137.9°C
• Appearance: /
• Density: 1.0505 (rough estimate)
• Vapor Pressure: 0.0017mmHg at 25°C
• Refractive Index: 1.4024 (estimate)
• PKA: 9.56±0.10(Predicted)
• CAS DataBase Reference: 5-Propyl-1,3-benzenediol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Propyl-1,3-benzenediol(500-49-2)
• EPA Substance Registry System: 5-Propyl-1,3-benzenediol(500-49-2)

Safety Data

• Hazardous Substances Data: 500-49-2(Hazardous Substances Data)

Usage

Description

A White to Brown crystalline solid.

Uses

5-Propylbenzene-1,3-diol is an intermediate used to prepare Cannabigerovarin (C175140) which stimulates thermosensitive transient receptor potential (TRP) channels of vanilloid type-4 (TRPV4)-mediated [Ca2+]i with moderate-high efficacy (30-60% of the effect of ionomycin) and potency (EC50 0.9-6.4 μM),

Synthesis

In a 100 mL round bottom flask, open to the atmosphere was added the crude product Benzene, 1,3-dimethoxy-5-propyl (0.736 g, 4.08 mmol, 1.0 equiv.) and a 1:1 mixture of glacial acetic acid (20 mL, 349.7 mmol, 17.4 M) and hydrobromic acid (48% in H2O, 20 mL, 368.3 mmol, 18.4 M). The reaction mixture was refluxed at 125 °C for 3 hours while stirring, or until the starting material was consumed via TLC analysis. At this point, the reaction was allowed to cool to room temperature and quenched by the addition of DI H2O. The biphasic solution was added to a separatory funnel, wherein the organic portion was extracted Et2O (ca. 3x 20 mL). The organic layers were then combined, neutralized with a concentrated sodium bicarbonate solution (ca. 30 mL), washed with a saturated brine solution (ca. 50 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford the final product without 5-Propyl-1,3-benzenediol (0.609 g, 99% yield) as a pale yellow oil.

Solubility in organics

5-Propyl-1,3-benzenediol is soluble in N,N-dimethylformamide, soluble in methanol, slightly soluble in glacial acetic acid, very slightly soluble in chloroform, almost insoluble in water.

InChI:InChI=1/C9H12O2/c1-2-3-7-4-8(10)6-9(11)5-7/h4-6,10-11H,2-3H2,1H3

Synthetic route

1,3-dimethoxy-5-propylbenzene (41395-10-2) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
With hydrogen bromide; acetic acid In water at 125℃; for 3h; Inert atmosphere;	99%
With hydrogen iodide; acetic anhydride for 1h; Heating;	90%
With hydrogen bromide; acetic acid for 3h; Heating;	70%

2-hydroxy-4-methoxy-6-propylbenzoic acid (6245-56-3) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
With hydrogen iodide

divaricatic acid (491-62-3) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
With potassium hydroxide
With hydrogen iodide
Multi-step reaction with 2 steps 1: natrium carbonate 2: hydriodic acid View Scheme
Multi-step reaction with 2 steps 1: natrium carbonate 2: alkalies View Scheme
Multi-step reaction with 2 steps 1: alkali 2: hydriodic acid View Scheme

2,4-dihydroxy-6-propylbenzoic acid (4707-50-0) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
With water
With alkalies

2-Bromo-3-hydroxy-5-propyl-cyclohex-2-enone (70336-33-3) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
With acetic acid

2,4-dihydroxy-6-propylbenzoic acid ethyl ester (21855-51-6) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
With sodium hydroxide In water Heating;

3-allylresorcinol (142039-78-9) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
With triphenyl phosphite; hydrogen In chloroform at 25℃; Rate constant; Mechanism;

1,3-dimethoxy-5-propylbenzene (41395-10-2) + hydrogen iodide (10034-85-2) → 5-propyl-1,3-benzenediol (500-49-2)

divaricatic acid (491-62-3) + alkali → 5-propyl-1,3-benzenediol (500-49-2) + carbon dioxide (124-38-9) + 2-hydroxy-4-methoxy-6-propylbenzoic acid (6245-56-3)

2-hydroxy-4-methoxy-6-propylbenzoic acid (6245-56-3) + hydrogen iodide (10034-85-2) → 5-propyl-1,3-benzenediol (500-49-2) + carbon dioxide (124-38-9) + methyl iodide (74-88-4)

divaricatic acid (491-62-3) + hydrogen iodide (10034-85-2) → 5-propyl-1,3-benzenediol (500-49-2) + carbon dioxide (124-38-9) + methyl iodide (74-88-4)

2,4-dihydroxy-6-propylbenzoic acid (4707-50-0) + water (7732-18-5) → 5-propyl-1,3-benzenediol (500-49-2)

2,4-dihydroxy-6-propylbenzoic acid (4707-50-0) + alkali → 5-propyl-1,3-benzenediol (500-49-2)

2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentyl-benzoyloxy)-6-propyl-benzoic acid (491-57-6) + aqueous KOH-solution → 5-propyl-1,3-benzenediol (500-49-2) + 2-hydroxy-4-methoxy-6-pentylbenzoic acid (52189-68-1)

3,5-dimethoxybenzyl alcohol (705-76-0) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: Et3N / tetrahydrofuran / 1 h / 0 - 20 °C 2: 62 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 3: 69 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 4: 60 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 5: 70 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

1-(3,5-dimethoxyphenyl)propan-2-ol (79859-93-1) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 2: 60 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 3: 70 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

3,5-dimethoxybenzyl trimethylsilyl ether (185249-83-6) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 2: 69 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 3: 60 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 4: 70 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

Methanesulfonic acid 2-(3,5-dimethoxy-phenyl)-1-methyl-ethyl ester (185249-88-1) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 2: 70 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

3,5-dimethoxybenzaldehdye (7311-34-4) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 2: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 3: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme
Multi-step reaction with 3 steps 1: diethyl ether / 1 h / 0 °C 2: hydrogen; palladium 10% on activated carbon; sulfuric acid / ethanol / 4 h / 3040.2 Torr 3: boron tribromide / dichloromethane / 2 h / -15 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 2 h 3.1: acetic acid; hydrogen bromide / water / 3 h / 125 °C / Inert atmosphere View Scheme

1-(3,5-dimethoxy-phenyl)-propan-1-ol (203912-55-4) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 2: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon; sulfuric acid / ethanol / 4 h / 3040.2 Torr 2: boron tribromide / dichloromethane / 2 h / -15 - 20 °C / Inert atmosphere View Scheme

3,5-dimethoxybenzoic acid (1132-21-4) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 89 percent / (COCl)2 / benzene / 2 h, room t., 1 h, reflux 2: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 3: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 4: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 5: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme
Multi-step reaction with 8 steps 4: 28.8 g / fluoroboric acid, sodium nitrite / H2O 5: 7.6 g / warming, distillation 6: 1.) lithium / 1.) ether, 2 h 7: Cu-quinoline 8: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 7 steps 4: 28.8 g / fluoroboric acid, sodium nitrite / H2O 5: 7.6 g / warming, distillation 6: 63.5 percent / lithium chips / diethyl ether / 0.5 h 7: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 3 steps 1: 85 percent / diethyl ether / 1.) from -78 deg C to 0 deg C , 1.5 h, 2.) RT, 18 h 2: 1.) H2N4*H2O, 2.) KOH / 1.) EtOH, reflux, 6 h, 2.) 230 deg C, 0.5 h 3: 90 percent / Ac2O, HI / 1 h / Heating View Scheme
Multi-step reaction with 6 steps 1: thionyl chloride; N,N-dimethyl-formamide / toluene / 6 h / 100 °C 2: triethylamine / dichloromethane / 0 °C 3: 2-methyltetrahydrofuran / 5 h / 0 °C 4: hydrazine hydrate / ethanol / 6 h / Reflux 5: potassium hydroxide / 0.5 h / 230 °C 6: pyridine hydrochloride / 4 h / 200 °C View Scheme

3,5-dimethoxybenzoyl chloride (17213-57-9) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 2: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 3: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 4: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme
Multi-step reaction with 7 steps 3: 28.8 g / fluoroboric acid, sodium nitrite / H2O 4: 7.6 g / warming, distillation 5: 1.) lithium / 1.) ether, 2 h 6: Cu-quinoline 7: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 6 steps 3: 28.8 g / fluoroboric acid, sodium nitrite / H2O 4: 7.6 g / warming, distillation 5: 63.5 percent / lithium chips / diethyl ether / 0.5 h 6: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 0 °C 2: 2-methyltetrahydrofuran / 5 h / 0 °C 3: hydrazine hydrate / ethanol / 6 h / Reflux 4: potassium hydroxide / 0.5 h / 230 °C 5: pyridine hydrochloride / 4 h / 200 °C View Scheme

ethyl 3,5-dimethoxybenzoate (17275-82-0) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 12 steps 1: 78 percent / hydrazine hydrate / 2 h / Heating 2: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C 3: 93 percent / toluene / 2.5 h / Heating 4: 8.7 g / sodium hydroxide (20percent) / 60 °C 8: 28.8 g / fluoroboric acid, sodium nitrite / H2O 9: 7.6 g / warming, distillation 10: 1.) lithium / 1.) ether, 2 h 11: Cu-quinoline 12: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 11 steps 1: 78 percent / hydrazine hydrate / 2 h / Heating 2: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C 3: 93 percent / toluene / 2.5 h / Heating 4: 8.7 g / sodium hydroxide (20percent) / 60 °C 8: 28.8 g / fluoroboric acid, sodium nitrite / H2O 9: 7.6 g / warming, distillation 10: 63.5 percent / lithium chips / diethyl ether / 0.5 h 11: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

3,5-Dihydroxybenzoic acid (99-10-5) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 9 steps 1: 84 percent / sodium hydroxide / heating 5: 28.8 g / fluoroboric acid, sodium nitrite / H2O 6: 7.6 g / warming, distillation 7: 1.) lithium / 1.) ether, 2 h 8: Cu-quinoline 9: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 8 steps 1: 84 percent / sodium hydroxide / heating 5: 28.8 g / fluoroboric acid, sodium nitrite / H2O 6: 7.6 g / warming, distillation 7: 63.5 percent / lithium chips / diethyl ether / 0.5 h 8: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

3,5-dimethoxybenzamide (17213-58-0) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 6 steps 2: 28.8 g / fluoroboric acid, sodium nitrite / H2O 3: 7.6 g / warming, distillation 4: 1.) lithium / 1.) ether, 2 h 5: Cu-quinoline 6: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 5 steps 2: 28.8 g / fluoroboric acid, sodium nitrite / H2O 3: 7.6 g / warming, distillation 4: 63.5 percent / lithium chips / diethyl ether / 0.5 h 5: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

2,4-dimethoxy-6-propylbenzoic acid (52189-64-7) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Cu-quinoline 2: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

azido(3,5-dimethoxyphenyl)methanone (75996-26-8) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 10 steps 1: 93 percent / toluene / 2.5 h / Heating 2: 8.7 g / sodium hydroxide (20percent) / 60 °C 6: 28.8 g / fluoroboric acid, sodium nitrite / H2O 7: 7.6 g / warming, distillation 8: 1.) lithium / 1.) ether, 2 h 9: Cu-quinoline 10: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 9 steps 1: 93 percent / toluene / 2.5 h / Heating 2: 8.7 g / sodium hydroxide (20percent) / 60 °C 6: 28.8 g / fluoroboric acid, sodium nitrite / H2O 7: 7.6 g / warming, distillation 8: 63.5 percent / lithium chips / diethyl ether / 0.5 h 9: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

3,5-dimethoxy-benzoic acid hydrazide (51707-38-1) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 11 steps 1: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C 2: 93 percent / toluene / 2.5 h / Heating 3: 8.7 g / sodium hydroxide (20percent) / 60 °C 7: 28.8 g / fluoroboric acid, sodium nitrite / H2O 8: 7.6 g / warming, distillation 9: 1.) lithium / 1.) ether, 2 h 10: Cu-quinoline 11: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 10 steps 1: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C 2: 93 percent / toluene / 2.5 h / Heating 3: 8.7 g / sodium hydroxide (20percent) / 60 °C 7: 28.8 g / fluoroboric acid, sodium nitrite / H2O 8: 7.6 g / warming, distillation 9: 63.5 percent / lithium chips / diethyl ether / 0.5 h 10: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

3,5-dimethoxyfluorobenzene (52189-63-6) → 5-propyl-1,3-benzenediol (500-49-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) lithium / 1.) ether, 2 h 2: Cu-quinoline 3: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: 63.5 percent / lithium chips / diethyl ether / 0.5 h 2: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

5-propyl-1,3-benzenediol (500-49-2) → 4,6-dibromo-5-propylbenzene-1,3-diol

Conditions	Yield
Stage #1: 5-propyl-1,3-benzenediol With bromine In dichloromethane at -50℃; for 0.5h; Stage #2: With sodium thiosulfate In dichloromethane; water at 0℃; Temperature;	82%

C18H8F2N4O10 (937720-91-7) + 5-propyl-1,3-benzenediol (500-49-2) → C27H18N4O12 (937720-92-8)

Conditions	Yield
With triethylamine In acetonitrile at 70℃; for 8h;	69%

diethyl 2-acetylglutarate (1501-06-0) + 5-propyl-1,3-benzenediol (500-49-2) → 3-(5-hydroxy-4-methyl-2-oxo-7-propyl-2H-chromen-3-yl)-propionic acid ethyl ester (468095-79-6)

Conditions	Yield
With trichlorophosphate	61%

5-propyl-1,3-benzenediol (500-49-2) + 4-benzyloxy-2-hydroxy-6-pentylbenzoic acid (53530-19-1) → 4-Benzyloxy-2-hydroxy-6-pentyl-benzoic acid 3-hydroxy-5-propyl-phenyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In toluene for 47h; Ambient temperature;	58%

5-propyl-1,3-benzenediol (500-49-2) + (+)-cis-piperityl acetate → cannabidivarin (24274-48-4) + C19H26O2

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane for 0.116667h; Flow reactor;	A 56% B 30%

5-propyl-1,3-benzenediol (500-49-2) + 2-hydroxy-4-methoxy-6-propylbenzoic acid (6245-56-3) → 3'-hydroxy-5'-propylphenyl 2-hydroxy-4-methoxy-6-propylbenzoate + depsidellin D

Conditions	Yield
With dicyclohexyl-carbodiimide In toluene for 120h; Ambient temperature;	A 38% B 13%

5-propyl-1,3-benzenediol (500-49-2) + (-)-trans-Isopiperitenol (74410-00-7) → 2-((1S,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)-5-propylbenzene-1,3-diol + C29H40O2 + C19H26O2

Conditions	Yield
With aluminum oxide; boron trifluoride diethyl etherate In dichloromethane for 0.00277778h; Inert atmosphere; Reflux;	A 37% B 12% C 18%

5-propyl-1,3-benzenediol (500-49-2) + (S)-cis-Verbenol (18881-04-4) → Propyl-delta(8)-tetrahydrocannabiol (31262-38-1)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 0 - 20℃; for 3h;	20%

hydrogen cyanide (74-90-8) + 5-propyl-1,3-benzenediol (500-49-2) → 2,4-dihydroxy-6-propylbenzaldehyde (37455-87-1)

Conditions	Yield
With diethyl ether durch Erhitzen des Reaktionsprodukts mit Wasser;

5-propyl-1,3-benzenediol (500-49-2) → 2,4,6-tribromo-5-propyl-resorcinol

Conditions	Yield
With bromine; acetic acid

5-propyl-1,3-benzenediol (500-49-2) + acetic anhydride (108-24-7) → 1,3-diacetoxy-5-propyl-benzene

Conditions	Yield
With sodium acetate at 85℃;
With pyridine Acetylation;

5-propyl-1,3-benzenediol (500-49-2) + ethyl 4-methyl-2-cyclohexanone-1-carboxylate (13537-82-1) → 1-hydroxy-9-methyl-3-propyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one (41516-21-6)

Conditions	Yield
With trichlorophosphate; benzene

5-propyl-1,3-benzenediol (500-49-2) + (+-)-pulegone → (R)-6,6,9-trimethyl-3-propyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-1-ol

Conditions	Yield
With trichlorophosphate; benzene

5-propyl-1,3-benzenediol (500-49-2) + zinc cyanide → 2,4-dihydroxy-6-propylbenzaldehyde (37455-87-1)

Conditions	Yield
With hydrogenchloride; diethyl ether durch Erhitzen des Reaktionsprodukts mit Wasser;

5-propyl-1,3-benzenediol (500-49-2) + pulegone (89-82-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) + benzene (71-43-2) → (+)(R)-1-hydroxy-6.6.9-trimethyl-3-propyl-7.8.9.10-tetrahydro-6H-benzochromene

5-propyl-1,3-benzenediol (500-49-2) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) + benzene (71-43-2) + 2-oxo-4-methyl-cyclohexane-carboxylic acid-(1)-ethyl ester → 1-hydroxy-9-methyl-3-propyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one (41516-21-6)

hydrogenchloride (7647-01-0) + diethyl ether (60-29-7) + 5-propyl-1,3-benzenediol (500-49-2) + zinc cyanide → 2,4-dihydroxy-6-propylbenzaldehyde (37455-87-1)

Conditions	Yield
Kochen des Reaktionsprodukts mit Wasser;

Upstream product

• 41395-10-2 1,3-dimethoxy-5-propylbenzene 
• 491-62-3 divaricatic acid 
• 10034-85-2 hydrogen iodide 
• 27871-91-6 methyl 6-n-propyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate 
• 14615-72-6 3,5-dibenzyloxybenzaldehyde 
• 21855-51-6 2,4-dihydroxy-6-propylbenzoic acid ethyl ester 
• 6245-56-3 2-hydroxy-4-methoxy-6-propylbenzoic acid 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 155586-39-3 (3,5-dimethoxyphenyl)-N-methoxy-N-methylcarboxamide 
• 502924-54-1 3-(3,5-dimethoxy-phenyl)-2-methyl-3-oxo-propionic acid ethyl ester 
• 41564-88-9 1-(3',4',5'-trimethoxyphenyl)propane 
• 41497-31-8 3,5-dimethoxyphenyl ethyl ketone 
• 54132-76-2 3,5-dimethoxyphenyl isocyanate 
• 10272-07-8 3.5-dimethoxyaniline 

Downstream Products

• 37455-87-1 2,4-dihydroxy-6-propylbenzaldehyde 
• 28172-17-0 (6aS,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 31262-38-1 3-norpentyl-3-propyl-Δ⁸-tetrahydrocannabinol 
• 24274-48-4 cannabidivarin 
• 41408-19-9 2-methyl-2-(4-methylpent-3-enyl)-7-propyl-5-chromenol 
• 33745-21-0 cannabivarin 
• 64924-07-8 6-carboxylic acid-2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-propyl-benzene-1,3-diol 
• 55824-11-8 CBGV 
• 31262-37-0 tetrahydrocannabivarin 

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(?)-Cannabidiol [(?)-CBD] has recently gained prominence as a treatment for neuro-inflammation and other neurodegenerative disorders; interest is also developing in its synthetic enantiomer, (+)-CBD, which has a higher affinity to CB1/CB2 receptors than the natural stereoisomer. We have developed an inexpensive, stereoselective route to access ent-CBD derivatives using (+)-carvone as a starting material. In addition to (+)-CBD, we report the first syntheses of (+)-cannabidivarin, (+)-cannabidiphorol as well as C-6/C-8 homologues.

PROCESS FOR THE PRODUCTION OF CANNABIDIOL AND DELTA-9-TETRAHYDROCANNABINOL

The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.