Hydrofluoric Acid → HCID 15430759, compound

HRID 1739602Notes

Reaction equation

HRID 1739602 reaction equation
[CH:1](=[C:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH:17]=[CH2:18])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH2:2][CH:3]=[CH2:4].[FH:19].C(=O)([O-])O.[Na+]>ClCCl.N1C=CC=CC=1>[CH2:1]([C:5]1([F:19])[CH2:6][CH2:7][CH:8]([CH:11]2[CH2:12][CH2:13][CH:14]([CH:17]=[CH2:18])[CH2:15][CH2:16]2)[CH2:9][CH2:10]1)[CH2:2][CH:3]=[CH2:4]

Participants

6

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 21835877HCID 21835877, compound

Product 1

HCID 15430759HCID 15430759, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

20.6 g of 4'-but-3-enylidene-4-vinylbicyclohexyl in 40 ml of dichloromethane were cooled to -25° C. 7.523 ml of a 70% solution of hydrogen fluoride in pyridine were then added dropwise with stirring, and the mixture was stirred at -25° C. for 30 minutes and then at RT for a further 8 hours. The reaction solution was poured into a suspension of 40 g of sodium hydrogencarbonate and 800 g of ice-water. The mixture was extracted with three times 150 ml of hexane. The combined organic extracts were washed once with 50 ml of sodium chloride solution, dried using sodium sulphate, filtered and evaporated to a residue. Crystallization from pentane at -25° C. gave 4-but-3-enyl-4-fluoro-4'-vinylbicyclohexyl (C 13 SmB 37 N 80 I, Δn=0.049, Δε=-1.8, viscosity=13 mm2).

Workup

  1. stirringthe mixture was stirred at -25° C. for 30 minutes
  2. extractionThe mixture was extracted with three times 150 ml of hexane
  3. washThe combined organic extracts were washed once with 50 ml of sodium chloride solution
  4. customdried
  5. filtrationfiltered
  6. customevaporated to a residue
  7. customCrystallization from pentane at -25° C.

Sources & evidence

ORD record
ord-f39255a0b0f8454ea213b0f9bccd0583
Source dataset
uspto-grants-1999_10
Patent number
US05968410

Reaction notes

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