Hydrochloric Acid → HCID 59408361, compound

HRID 2389209Notes

Reaction equation

HRID 2389209 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]3[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Br[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Mg].[Cl-].[NH4+].Cl>C1COCC1>[O:1]1[C:5]2([CH2:6][CH2:7][CH:8]([CH:11]3[CH2:16][CH2:15][C:14]([C:25]4[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][CH3:19])=[CH:23][CH:24]=4)([OH:17])[CH2:13][CH2:12]3)[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 12503(3-Bromopropyl)benzeneHCID 25517Ammonium ChlorideHCID 8109134-(1,4-Dioxa-spiro(4.5)dec-8-yl)-cyclohexanoneHCID 5462224Magnesium

Product 1

HCID 59408361HCID 59408361, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 160 g (0.67 mol) of 4-(1,4-dioxaspiro[4.5]dec-8-yl)cyclohexanone in 600 ml of THF is added to a solution of the Grignard reagent generated from 147 g (0.74 mol) of p-bromopropylbenzene and 18.0 g (0.74 mol) of magnesium turnings (400 ml of THF). When the addition is complete, the mixture is heated under reflux for 1 h, and sat. ammonium chloride soln. is added. The mixture is acidified using dil. hydrochloric acid and extracted a number of times with MTBE. The combined organic phases are washed with water, and the solution is dried using sodium sulfate. The crude product obtained after removal of the solvents is used without further purification.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 1 h
  4. additionis added
  5. extractionextracted a number of times with MTBE
  6. washThe combined organic phases are washed with water
  7. customthe solution is dried

Sources & evidence

ORD record
ord-f9b3531d992c4f89bd19f449c6ba2345
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

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