Hydrochloric Acid → HCID 69104144, compound

HRID 2220411Notes

Reaction equation

HRID 2220411 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[C:10]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:9]=1.Cl>O1CCCC1>[Br:7][C:8]1[CH:16]=[CH:15][C:11]([CH2:12][OH:13])=[C:10]([O:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 24824481HCID 24824481, compound

Product 1

HCID 69104144HCID 69104144, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (2.54 g) in tetrahydrofuran (50 ml) was added dropwise a solution of 4-bromo-2-(cyclohexyloxy)benzoic acid (10 g) in tetrahydrofuran (50 ml) at 5° C. under nitrogen, and the mixture was stirred at room temperature for 2.5 hours. The resulting mixture was poured into 1N hydrochloric acid and the aqueous layer was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid, aqueous-sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10:1 to 5:1) to give (4-bromo-2-cyclohexyloxyphenyl)methanol (5.47 g).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed successively with 1N hydrochloric acid
  3. dry with materialaqueous-sodium bicarbonate and brine, dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-5717fb4ea3ed477581f0899a00541a3e
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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