Phosphoric Acid → 1-Naphthalenecarbonitrile, 1,2,3,4-tetrahydro-4,4-dimethyl-

HRID 1979508Notes

Reaction equation

P(=O)(O)(O)O.[CH3:6][C:7]([CH3:19])=[CH:8][CH2:9][CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:11]#[N:12]>C1(C)C=CC=CC=1>[CH3:6][C:7]1([CH3:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:10]([C:11]#[N:12])[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 100 °C

Procedure

46.3 g of 85% phosphoric acid, 46.3 g of polyphosphoric acid, 250 ml of toluene and 92.6 g of 5-methyl-2-phenyl-4-hexene nitrile are mixed together and heated at 100° C. while stirring for 3 hours. The mixture is then poured on to ice. The mixture is now extracted with ether, washed with water, with 10% sodium carbonate solution and again with water until neutral, dried, evaporated and distilled in vacuo. There are obtained 85.3 g of 1,1-dimethyl-4-cyano-tetralin of boiling point 114° C./2 mm; nD20 =1.5351; yield 92%. Odour: pleasantly fruity, tobacco-like, after straw with a resemblance of patchouli and amber.

Workup

additionThe mixture is then poured on to ice
extractionThe mixture is now extracted with ether
washwashed with water, with 10% sodium carbonate solution and again with water until neutral,
customdried
customevaporated
distillationdistilled in vacuo

Sources & evidence

ORD record: ord-57004db5a3d140a18aadce5091f1aec8
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04481133

Reaction notes

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