Water → 2-[3-(Benzyloxy)phenyl]octan-2-ol

HRID 2199009Notes

Reaction equation

HRID 2199009 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]C.[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=1)=[O:11].O.[CH2:27]([Mg]Br)CCCCC.[Cl-].[NH4+]>O1CCCC1.CCOCC>[CH2:19]([O:18][C:14]1[CH:13]=[C:12]([C:10]([CH3:27])([OH:11])[CH2:9][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 6

HCID 962WaterHCID 81011-BromohexaneHCID 25517Ammonium ChlorideHCID 986891-(3-(Phenylmethoxy)phenyl)ethan-1-oneHCID 5462224MagnesiumHCID 178444609HCID 178444609, compound

Product 1

HCID 130526942-[3-(Benzyloxy)phenyl]octan-2-olYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

To a slurry of 186 g. (7.65 mole) of magnesium in 3.5 l. of tetrahydrofuran was added 1.023 l. (7.29 mole) of 1-bromohexane over 2 hours. The resultant Grignard solution was allowed to cool to 25° C. A solution of 1.098 kg. (4.86 mole) of 3-benzyloxyacetophenone in 1 liter of tetrahydrofuran was added to the Grignard solution over a 3 hour period. The reaction temperature was maintained at 12°-18° C. with an ice bath. Upon completion of the addition the reaction was allowed to stir overnight at 25° C. A solution of 61.5 g. (3.42 mole) of water in 120 ml. tetrahydrofuran was added to the reaction over 15 minutes and, after stirring 20 minutes longer 0.440 l. (1.1 mole) of 2.5 M hexylmagnesium bromide in ether, was added. The reaction was stirred 20 hours longer and then quenched by slow addition to a mixture of 6 l. water and ice and 750 g. (14.2 mole) of ammonium chloride. The organic extract was removed and the aqueous extract was extracted with 1 liter of ether. The combined organic extract was washed with 1 liter of saturated sodium chloride, dried over magnesium sulfate and evaporated to yield 1.424 kg. (94%) of the title compound as an oil.

Workup

  1. temperatureThe reaction temperature was maintained at 12°-18° C. with an ice bath
  2. additionUpon completion of the addition the reaction
  3. stirringafter stirring 20 minutes longer 0.440 l
  4. stirringThe reaction was stirred 20 hours longer
  5. customquenched by slow addition to a mixture of 6 l
  6. extractionThe organic extract
  7. customwas removed
  8. extractionthe aqueous extract
  9. extractionwas extracted with 1 liter of ether
  10. extractionThe combined organic extract
  11. washwas washed with 1 liter of saturated sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. customevaporated
  14. customto yield 1.424 kg

Sources & evidence

ORD record
ord-e609f4b186de4c1184481673f08ff5b8
Source dataset
uspto-grants-1982_11
Patent number
US04360700

Reaction notes

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