22972-51-6

Basic information

• Product Name: (+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL
• Synonyms: (1S,4R) 1-METHYL-4-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-OL;(+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL;(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol;trans-Mentha-2,8-dien-1-ol;(1S,4R)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-2-eno;(1S,4R)-4-Isopropenyl-1-methylcyclohex-2-en-1-ol;2-Cyclohexen-1-ol,1-Methyl-4-(1-Methylethenyl)-, (1S,4R)-;(1S,4R)-1-methyl-4-prop-1-en-2-ylcyclohex-2-en-1-ol
• CAS NO: 22972-51-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• Mol File: 22972-51-6.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 216.873 °C at 760 mmHg
• Flash Point: 86.957 °C
• Appearance: /
• Density: 0.947 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Soluble), Methanol (Soluble)
• PKA: 14.66±0.40(Predicted)
• Water Solubility: 4.2g/L
• Stability: Light Sensitive
• CAS DataBase Reference: (+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL(22972-51-6)
• EPA Substance Registry System: (+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL(22972-51-6)

Safety Data

• Hazardous Substances Data: 22972-51-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 22972-51-6 differently. You can refer to the following data:
1. (+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL is an acetal reagent used in the synthesis of desoxy cannabidiols and THC (T293202) related psychoactive compounds. It is formed from (+)-Limonene using a photosynthesized O2 transfer.
2. 1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol is an acetal reagent used in the synthesis of desoxy cannabidiols and THC (T293202) related psychoactive compounds. It is formed from (+)-Limonene using a photosynthesized O2 transfer.

Synthetic route

C16H22O2S → (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
With piperidine In dimethyl sulfoxide at 170℃; for 4h;	75%

(1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide (1415961-21-5) → (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
at 180℃; under 1 Torr; Cope Elimination; Pyrolysis;	74%
With dihydrogen peroxide In ethanol; water at 150 - 162℃; Reflux; Schlenk technique; Glovebox; Inert atmosphere;	38.2 g

(1S,2S,4R)-2-phenylseleninyl-p-menth-8-en-1-ol (74756-11-9) → (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
In chloroform for 0.5h; Heating;	53%
In chloroform at 62℃; for 6h; Inert atmosphere;	512 g

(1S,2R,4R)-limonene-1,2-epoxide (6909-30-4) → (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
Stage #1: (1S,2R,4R)-limonene-1,2-epoxide With sodium tetrahydroborate; diphenyl diselenide for 2h; Heating; Stage #2: With dihydrogen peroxide for 7h; Heating; Further stages.;	31.6%
Multi-step reaction with 2 steps 1.1: H2O / 18 h / 150 °C 2.1: H2O2 / H2O / 18 h / 20 °C 2.2: 150 - 180 °C View Scheme
Multi-step reaction with 3 steps 1: H2O / 150 °C / sealed vessel 2: 30percent H2O2 / H2O 3: pyrolysis View Scheme

D-limonene (5989-27-5) → (1R,4R)-p-mentha-2,8-dien-1-ol (52154-82-2) + (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
With oxygen; rose bengal In methanol at 0℃; for 8.5h; UV-irradiation;	A 5.3% B 13.4%
With air Erwaermen des Reaktionsprodukts mit wss. Natriumsulfit-Loesung;
(i) O2, MeOH, (irradiation), (ii) LiAlH4, Et2O; Multistep reaction;
(i) O2, rose bengal, MeOH, (irradiation), (ii) LiAlH4, Et2O; Multistep reaction;
With air Erwaermen des Reaktionsprodukts mit wss. Natriumsulfit-Loesung;

D-limonene (5989-27-5) → (4R,6R)-carveol (99-48-9, 1197-06-4, 1197-07-5, 2102-58-1, 2102-59-2, 5157-78-8, 5503-11-7, 7632-16-8, 18383-51-2) + (-)-trans-carveol (18383-51-2) + (1R,4R)-p-mentha-2,8-dien-1-ol (52154-82-2) + (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6) + p-Menthadiene-<1(7),8>-trans-ol-(2) (2102-62-7) + p-Menthadiene<1(7),8>-cis-ol-(2) (10374-04-6)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; air; zinc 5,10,15,20-tetraphenylporphyrin; triphenylphosphine In benzene for 3h; Irradiation; multistep reaction: photosensitized oxygenation of olefines;
With sodium tetrahydroborate; tetraphenylporphyrine; oxygen Product distribution; 1.) acetonitrile, irradiation, 2.) methanol; other sensitizers;	A 5 % Chromat. B 7 % Chromat. C 9 % Chromat. D 40 % Chromat. E 16 % Chromat. F 23 % Chromat.
With oxygen; fullerene-C60 In toluene at 0 - 10℃; for 4h; Product distribution; Irradiation; other sensitizer in other solvent;

limonene. (138-86-3) → (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
With oxygen Irradiation;

D-limonene (5989-27-5) → (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
With oxygen Irradiation;
Multi-step reaction with 4 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1.5 h / -5 - 20 °C 2: water / 18 h / 20 °C / Reflux 3: dihydrogen peroxide / water; acetonitrile / 2 h / 20 °C / Cooling with ice 4: 180 °C / 1 Torr / Pyrolysis View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C 2.1: sodium tetrahydroborate / ethanol / 1 h / 8 °C / Inert atmosphere 2.2: 4 h / 8 - 80 °C / Inert atmosphere 3.1: dihydrogen peroxide / ethanol; tetrahydrofuran / 6 h / 6 - 20 °C / Inert atmosphere 4.1: chloroform / 6 h / 62 °C / Inert atmosphere View Scheme

(+)-trans-N.N-Dimethylamino-2-p-menthen-8-ol-1-N-oxyd → (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
at 140℃;

(1S,2S,4R)-4-Isopropenyl-1-methyl-2-nitroso-cyclohexanol → (1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6)

Conditions	Yield
pyrolysis; Yield given;

Upstream product

• 5989-27-5 D-limonene 
• 74756-11-9 (1S,2S,4R)-2-phenylseleninyl-p-menth-8-en-1-ol 
• 138-86-3 limonene. 
• 1686-14-2 α-pinene epoxide 
• 1195-92-2 Limonene oxide 
• 106-24-1 Geraniol 
• 106-25-2 Nerol 
• 74756-09-5 1α-hydroxy-2β-phenylseleno-trans-p-menth-8-ene 
• 34837-55-3 Phenylselenyl bromide 
• 521925-06-4 (1S,4R)-2-chloro-4-(1-methylvinyl)-1-methylcyclohexanol 
• 5989-54-8 (-)-(S)-limonene 
• 74756-09-5 (1S,2S,4R)-4-Isopropenyl-1-methyl-2-phenylselanyl-cyclohexanol 
• 1415961-21-5 (1S,2S,5R)-2-hydroxy-N,N,2-trimethyl-5-(prop-1-en-2-yl)cyclohexanamineoxide 

Downstream Products

• 111319-95-0 (5R)-2-methyl-5-(1-methylethenyl)-1,3-cyclohexadiene 
• 22663-41-8 (6aR,10aR)-6,6,9-trimethyl-3-(2-methylhexan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 1381973-51-8 [(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-4-pentylbenzene 
• 1415961-22-6 diethyl 2-[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-5-pentylphenyl phosphate 
• 63998-82-3 (3R,4R)-ω-carboxy-p-cannabidiol 
• 120467-25-6 (3R,4R)-ω-carboxy-o-cannabidiol 
• 120467-26-7 5-[3,5-Dihydroxy-2,4-bis-((1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-phenyl]-pentanoic acid 
• 61187-22-2 1-(c-4'-hydroxy-4'-methyl-r-1'-cyclohexyl)ethanone 
• 74333-68-9 (3R,4R)-ω-methoxycarbonyl-p-cannabidiol 
• 74333-67-8 (3R,4R)-ω-methoxycarbonyl-o-cannabidiol 
• 120467-27-8 5-[3,5-Dihydroxy-2,4-bis-((1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-phenyl]-pentanoic acid methyl ester 
• 1972-05-0 Cannabidiol monomethyl ether 
• 120467-11-0 (6aR,10aR)-6,6,9-trimethyl-3-phenethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 120467-12-1 (6aR,10aR)-6,6,9-trimethyl-3-phenethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol 

Relevant articles and documents

Highly efficient catalysts in directed oxygen-transfer processes: Synthesis, structures of novel manganese-containing heteropolyanions, and applications in regioselective epoxidation of dienes with hydrogen peroxide

A series of novel manganese(II)-substituted polyoxometalates, [(M(II)(H2O)3)2(WO2)2(BiW9O33)2] 10-(1), [(Mn(II)(H2O))3(SbW9O33)2]12- (2), and [(Mn(II)(H2O)3)2(Mn(II)(H2O)2)2(TeW9O33)2]8- (3), were synthesized and characterized by X-ray structure analyses. The use of these oxidatively and solvolytically stable heteropolyanions as homogeneous catalysts for the epoxidation of dienes was investigated by gas chromatography/mass spectrometry, IR spectroscopy, UV-visible studies, and cyclic voltammetric measurements. The catalytic performance is exemplified by the model substrate (R)-(+)-limonene, at ambient temperatures in a biphasic system, with excellent regioselectivities, >99%, and very high turnovers even with only a small molar excess of hydrogen peroxide.

Preparation method of (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol

The invention relates to a preparation method of (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol, and belongs to the technical field of organic solvents. The preparation method comprises the following steps: reacting limonene with a halogenating reagent to obtain an intermediate shown in a formula (1), then reacting the intermediate shown in the formula (1) with a tertiary amine compound to obtain an intermediate shown in a formula (2), and finally carrying out a pyrolysis elimination reaction on the intermediate shown in the formula (2) to obtain (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol. The preparation method has the advantages of mild conditions, no need of an oxidation process of hydrogen peroxide with high preparation condition requirements and high safety risk, no need of an expensive catalyst, high yield, high product purity, simple steps, and suitableness for industrial production.

Preparation method of (1S, 4R)-1-methyl-4-(1-methyl vinyl)-2-cyclohexene-1-alcohol

The invention discloses a preparation method of (1S, 4R)-1-methyl-4-(1-methyl vinyl)-2-cyclohexene-1-alcohol, which comprises the following steps: by using D-limonene as a raw material, carrying out double bond addition and hydroxyl protection to obtain an intermediate compound; and carrying out elimination reaction and continuing deprotection to finally prepare the product. The method has the advantages of two-step continuous reaction, short process route and few byproducts, the obtained product has high chiral selectivity, and the yield is up to 70% or above and is greatly improved comparedwith the existing process.