Hydrochloric Acid → HCID 178444350, compound

HRID 1742788Notes

Reaction equation

HRID 1742788 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Mg].[CH2:10]([C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[C:22](=O)[CH2:23][CH2:24][CH2:25][CH:26]=2)[CH2:17][CH2:16]1)[CH2:11][CH2:12][CH2:13][CH3:14].Cl.C([O:31]CC)C>>[CH2:10]([C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[CH2:22][CH2:23][C:24]([C:2]3[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=3)([OH:31])[CH2:25][CH:26]=2)[CH2:17][CH2:16]1)[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 78041,4-DibromobenzeneHCID 5462224MagnesiumHCID 178444303HCID 178444303, compound

Product 1

HCID 178444350HCID 178444350, compound

Procedure

A solution of 7.2 g of p-dibromobenzene in 40 ml of anhydrous diethyl ether was added dropwise under stirring at 10°-15° C. to 0.66 g of magnesium metal powder, followed by reaction at room temperature for one hour so that a Grignard reagent was formed. After 5 g of trans-4-pentylcyclohexylcyclohexenone 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 added dropwise to the reaction mixture, followed by the extraction of the reaction mixture with diethyl ether. After the extract was washed with saturated NaCl, anhydrous sodium sulfate was added to dry the extract. The diethyl ether was distilled off under reduced pressure, whereby 1-(trans-4-pentylcyclohexyl)-4-(4-bromophenyl)-4-hydroxycyclohexene was obtained as a crude reaction product.

Workup

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

Sources & evidence

ORD record
ord-214b2b73b64f47fe9780076cf54620a6
Source dataset
uspto-grants-1994_08
Patent number
US05342546

Reaction notes

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