Hydrochloric Acid → HCID 59408353, compound

HRID 2389205Notes

Reaction equation

HRID 2389205 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[CH2:14]([CH:17]1[CH2:22][CH2:21][CH:20]([CH:23]2[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]2)[CH2:19][CH2:18]1)[CH2:15][CH3:16].Cl>CCOCC.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:26]2([OH:29])[CH2:25][CH2:24][CH:23]([CH:20]3[CH2:21][CH2:22][CH:17]([CH2:14][CH2:15][CH3:16])[CH2:18][CH2:19]3)[CH2:28][CH2:27]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78041,4-DibromobenzeneHCID 4354185[1,1'-Bicyclohexyl]-4-one,4'-propyl-,HCID 178418339Butyllithium

Product 1

HCID 59408353HCID 59408353, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

106 g (0.45 mol) of 1,4-dibromobenzene are initially introduced in 400 ml of Et2O at −45° C., and 275 ml (0.45 mol) of n-BuLi (15% soln. in hexane) are metered in. After 30 min at this temperature, a solution of 100 g (0.45 mol) of 4′-propylbicyclohexyl-4-one in 200 ml of Et2O is added dropwise, and the mixture is warmed to 0° C. After 1 h, water and dil. hydrochloric acid are added to the batch, and the organic phase is separated off. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with water and subsequently dried using sodium sulfate. The solution is concentrated to completion, and the residue is used without further purification for the following reaction.

Workup

  1. waitAfter 1 h
  2. customthe organic phase is separated off
  3. extractionThe aqueous phase is extracted with MTBE
  4. washthe combined organic phases are washed with water
  5. customsubsequently dried
  6. concentrationThe solution is concentrated to completion
  7. customthe residue is used without further purification for the following reaction

Sources & evidence

ORD record
ord-e17d784521c6422d81174e6cf018382c
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

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