Hydrochloric Acid → 4-Ethynyl-4,4'-dipentylbicyclohexyl

HRID 380254Notes

Reaction equation

HRID 380254 reaction equation
CC([O-])(C)C.[K+].Br[CH:8]([C:11]1([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:16][CH2:15][CH:14]([CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)[CH2:9]Br.O.Cl>C(O)(C)(C)C>[C:8]([C:11]1([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:12][CH2:13][CH:14]([CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:19][CH2:18]2)[CH2:15][CH2:16]1)#[CH:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 154568254-(1,2-Dibromoethyl)-4,4'-dipentylbicyclohexylHCID 23665647Potassium tert-butoxide

Product 1

HCID 154519764-Ethynyl-4,4'-dipentylbicyclohexyl

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

32.48 g of KOtBu are added at RT to 47.50 g of 4-(1,2-dibromoethyl)-4,4′-dipentylbicyclohexyl in 150 ml of tert-butanol. The mixture is heated to 60° C. and stirred at this temperature overnight. Water is subsequently added to the reaction mixture, which is acidified with dilute hydrochloric acid and subjected to conventional work-up, giving 4-ethynyl-4,4′-dipentylbicyclohexyl (C 16 N 35 I, Δε−1.96, Δn 0.021).

Sources & evidence

ORD record
ord-55dfd87facee4c4690b6fcf51ed5c822
Source dataset
uspto-grants-2001_10
Patent number
US06303194B1

Reaction notes

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