ChemicalBook CAS DataBase List (1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol

(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol synthesis

8synthesis methods

Product Name:(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol
CAS Number:22972-51-6
Molecular formula:C10H16O
Molecular Weight:152.23

(+)-(1S,4R)-P-MENTHA-2,8-DIEN-1-OL can be used as an intermediate in organic synthesis for the synthesis of cannabidiol.

Cyclohexanol, 2-(dimethyloxidoamino)-1-methyl-4-(1-methylethenyl)-, (1S,2S,4R)-

1415961-21-5
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(1S,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-2-enol

22972-51-6
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$18.00/1g

Yield:22972-51-6 74%

Reaction Conditions:

at 180; under 1 Torr;Pyrolysis;Cope Elimination;

Steps:

1S,4R-4-Isopropenyl-1-methyl-cyclohex-2-en-1-ol (p-mentha-2,8-dien-1-ol) 6
The 1S,2S,5R-N,N,2-trimethyl-2-hydroxy-5-isopropenylcyclohexamine oxide (1.430 g, 6.7 mmol) was heated in a Kugelrohr oven at 180 C under vacuum (1 mmHg) until all the solid residue had disappeared. The yellow distillate (1.317 g) was subjected to flash chromatography (2:3, diethyl ether: hexane) to obtain the colorless oil of 6 (0.752g, 74%). Rf 0.32 (2:3 Et2O : hexane); [α]_D²⁶: +60 (1.0, CHCl₃), lit.4 [α]_D²³: +53.8 (CHCl₃); IR (SeZn): 3354 (m, broad, O-H), 2967 (m, C-H), 2935 (m, C-H), 2861 (m, C-H), 1644 (m, C=C), 1105 (s, C-O), 888 (s, C=C-H bend), 736 (s, C=C-H bend) cm-1; 1H NMR (500 MHz, CDCl₃): δ 5.70 (1H, ddd, 3JH2-H3 10.0 Hz, 4JH2-H4 2.4 Hz, 4JH2-H6 1.4 Hz, H2), 5.65 (1H, ddd, 3JH3-H2 10.0 Hz, 3JH3-H4 2.4 Hz, 4JH3-H5 0.8 Hz, H3), 4.78 (1H, quin, 4JH9b-H10≈4JH9b-H4 1.6 Hz, H9b), 4.74 (1H, quin, 4JH9a-H10≈4JH9a-H4 0.88 Hz, H9a), 2.65 (1H, m, H4), 1.88-1.73 (2H, m, H5eq, H6eq), 1.73 (3H, s, H10), 1.66-1.51 (3H, m, H5ax, H6ax, OH), 1.29 (3H, s, H7) ppm; 13C NMR (125 MHz, CDCl₃): 148.3 (C8), 134.1 (C2), 132.3 (C3), 110.7 (C9), 67.6 (C1), 43.6 (C4), 36.9 (C6), 29.6 (C7), 25.0 (C5), 21.0 (C10) ppm; LRMS (GC-MS): m/z 152 (M˙+, 2%), 134 ([M-H₂O]˙+, 11%), 119 [M-CH₃-H₂O]˙+, 32%), 91 (100%), 79 (37%), 77 (46%); Anal. (C₁₀H₁₆O) Calc: C 78.90, H 10.59; Found: C 78.25, H 10.59, N <0.05.