Hydrochloric Acid → HCID 86759326, compound

HRID 2119281Notes

Reaction equation

HRID 2119281 reaction equation
[Mg].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:17]([CH:21]1[CH2:26][CH2:25][CH:24](C2CCC(=O)CC2)[CH2:23][CH2:22]1)[CH2:18][CH2:19][CH3:20].Cl>C1COCC1>[CH2:17]([CH:21]1[CH2:26][CH2:25][CH:24]([C:12]2[C:11]([C:10]3([OH:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[C:10]([O:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:23][CH2:22]1)[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5462224MagnesiumHCID 234403784'-Butyl[1,1'-bi(cyclohexane)]-4-one

Product 1

HCID 86759326HCID 86759326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the Grignard reagent which was prepared from 2.31 g (95.1 mmol) of dried magnesium and 25.0 g (95.0 mmol) of 4-benzyloxy-bromobenzene in 300 ml of THF, was added dropwise 100 ml of solution of 21.0 g (88.8 mmol) of 4-(4-n-butylcyclohexyl)-cyclohexanone in THF at room temperature, and the mixture was stirred at the same temperature for 12 hours. The reaction solution was added to 500 ml of 0.5N hydrochloric acid, the product thus formed was extracted with ether, the extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn, and then the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: toluene), the solvent was distilled off, and the residue was recrystallized from toluene to give 11.8 g (28.1 mmol) of 4-(4-(4-n-butyl-cyclohexyl(-1-hydroxycyclohexyl)-1-benzyloxybenzene. Yield of this compound based on 4-(4-n-butylcyclohexyl)cyclohexanone was 31.6%.

Workup

  1. customthe product thus formed
  2. extractionwas extracted with ether
  3. washthe extract was washed with saturated aqueous sodium bicarbonate solution and water in this turn
  4. distillationthe solvent was distilled off
  5. customAfter the residue was purified by column chromatography on silica gel (eluent: toluene)
  6. distillationthe solvent was distilled off
  7. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-a37f625a563c4112b9460929df0dc085
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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