Menthol → HCID 18469616, compound

HRID 2228362Notes

Reaction equation

[C:1]([C:3](=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH:22]1([CH3:32])[CH2:27]C[CH:25]([CH:28](C)[CH3:29])[CH:24](O)[CH2:23]1.C([O-])([O-])=O.[Na+].[Na+]>>[C:1]([C:3](=[C:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6][CH:7]1[CH:23]([CH:22]([CH3:32])[CH3:27])[CH2:24][CH2:25][CH:28]([CH3:29])[CH2:8]1)=[O:5])#[N:2]

Participants

Reactant 3

HCID 1254Menthol

HCID 10340Sodium Carbonate

HCID 243274Etocrylene

Product 1

HCID 18469616HCID 18469616, compoundYield 57%

Procedure

55.4 g (0.2 mol) of ethyl 2-cyano-3,3-diphenylacrylate (Uvinul 3035), 62.5 g of menthol and 4 g of Na2CO3 were reacted with one another at 185-200° C. with distillative removal of the ethanol formed, assisted by a stream of nitrogen. After about 6 h, the reaction mixture was cooled and distilled under reduced pressure, giving 44 g (57%) of menthyl 2-cyano-3,3-diphenylacrylate [λmax=300 nm, E11=351].

Workup

customwith distillative removal of the ethanol
customformed
temperaturethe reaction mixture was cooled
distillationdistilled under reduced pressure

Sources & evidence

ORD record: ord-bf4bdbd5276747da8a4bf9b1a8722bea
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06416773B2

Reaction notes

Loading…