Menthol → HCID 14639416, compound

HRID 542230Notes

Reaction equation

HRID 542230 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([OH:8])[CH:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.CC(C)([O-])C.[K+].F[C:19]1[CH:24]=[CH:23][C:22]([N+]([O-])=O)=[CH:21][CH:20]=1>C(OCC)(=O)C.C(O)(C)(C)C>[CH:2]1([CH3:1])[CH2:3][CH2:4][CH:5]([CH:9]([CH3:11])[CH3:10])[CH:6]([O:8][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7]1

Participants

6

Reactant 3

HCID 1254MentholHCID 9590p-FluoronitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 14639416HCID 14639416, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.9 g of 2,6-difluorobenzoylisocyanate were added to a solution of 2.47 g of 4-dl-menthyloxy-aniline in a mixture of 15 ml of diethyl ether and 15 ml of petroleum ether (60-80) while stirring at room temperature. After adding 35 ml of petroleum ether (60-80), stirring was continued for another hour, after which the formed prepcipitate was sucked off, washed with petroleum ether and dried. The desired product was obtained in a yield of 4.1 g; melting-point 189°-190° C. The starting aniline was obtained from the corresponding nitro compound by reduction with hydrogen under the influence of Raney nickel as a catalyst, ethyl acetate being used as a solvent. 1-Nitro-4-dl-menthyloxybenzene was prepared by reaction of dl-menthol with 1-fluoro-4-nitrobenzene in tert.-butanol as a solvent in the presence of potassium tert.-butoxide.

Sources & evidence

ORD record
ord-824df436b47d49d7ae370ff67769c344
Source dataset
uspto-grants-1987_04
Patent number
US04656193

Reaction notes

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