Hydrochloric Acid → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrile

HRID 1382423Notes

Reaction equation

HRID 1382423 reaction equation
Cl[CH:2](P(=O)(OCC)OCC)[C:3]1[CH:12]=[CH:11][C:10]2[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[CH:4]=1.[C:25]([C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1)#[N:26].Cl>CS(C)=O>[CH3:14][C:9]1([CH3:13])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:16])[C:5]2[CH:4]=[C:3]([C:2]#[C:31][C:30]3[CH:33]=[CH:34][C:27]([C:25]#[N:26])=[CH:28][CH:29]=3)[CH:12]=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 660424-CyanobenzaldehydeHCID 13604831Diethyl 1-chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)methylphosphonate

Product 1

HCID 136048264-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 13.8 g (0.123 mole) of potassium tert.-butylate in 65 ml of dimethyl sulfoxide was added dropwise in the course of 30 minutes to a solution of 22.6 g (0.06 mole) of diethyl 1-chloro-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-methylphosphonate (about 85% strength) and 7.86 g (0.06 mole) of 4-cyanobenzaldehyde in 190 ml of dry dimethyl sulfoxide at room temperature. Stirring was continued for 1 hour, after which the mixture was poured onto 1 liter of ice water and acidified with a little dilute hydrochloric acid, and the resulting crystals were filtered off under suction. Recrystallization from ethanol gave 9.2 g (49%) of the title compound of melting point 157° C.

Workup

  1. filtrationthe resulting crystals were filtered off under suction
  2. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-b5437446c46c44249e10468883003147
Source dataset
uspto-grants-1989_02
Patent number
US04806558

Reaction notes

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