Hydrochloric Acid → HCID 53652455, compound

HRID 1742793Notes

Reaction equation

HRID 1742793 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:8])[CH:7]=1.[Mg].[CH2:11]([CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH:18]=[CH:17]1)[CH2:12][CH2:13][CH2:14][CH3:15].Cl>C(OCC)C>[OH:22][C:19]1([C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=2)[CH2:20][CH2:21][CH:16]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:17]=[CH:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5462224MagnesiumHCID 13479951HCID 13479951, compound

Product 1

HCID 53652455HCID 53652455, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 30.1 g of 3,5-difluorobromobenzene in 90 ml of anhydrous diethyl ether was added dropwise under stirring at 15°-20° C. to 4.5 g of magnesium metal powder, followed by reaction at room temperature for one hour so that 3,5-difluoromagnesium bromobenzene (a Grignard reagent) was formed. After 20 g of 4-pentylcyclohexenone were added under stirring at -10° to 0° C. to the thus-formed Grignard reagent, they were reacted at room temperature for additional 1 hour. After the completion of the reaction, diluted hydrochloric acid was gradually added dropwise to the reaction mixture, followed by extraction with diethyl ether. After the extract was washed with saturated NaCl, anhydrous sodium sulfate was added to dry the extract. The resultant mixture was filtered and the solvent was distilled off from the filtrate under reduced pressure, whereby 1-(1-hydroxy-4-pentylcyclohexenyl)-3,5-difluorobenzene was obtained as a crude reaction product.

Workup

  1. customwas formed
  2. customwere reacted at room temperature for additional 1 hour
  3. additionwas gradually added dropwise to the reaction mixture
  4. extractionfollowed by extraction with diethyl ether
  5. washAfter the extract was washed with saturated NaCl, anhydrous sodium sulfate
  6. additionwas added
  7. customto dry the extract
  8. filtrationThe resultant mixture was filtered
  9. distillationthe solvent was distilled off from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-a7fda5fd42f548df974934871ff07c10
Source dataset
uspto-grants-1994_08
Patent number
US05342546

Reaction notes

Loading…