Hydrochloric Acid → 3-(4-Bromo-3-methyl-phenyl)-pentan-3-ol

HRID 1443327Notes

Reaction equation

HRID 1443327 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][C:3]=1[CH3:12].[Cl-].[Na+].[CH2:15]([Mg]Br)[CH3:16].Cl.O1CC[CH2:22][CH2:21]1>C(OCC)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])([CH2:15][CH3:16])[CH2:21][CH3:22])=[CH:4][C:3]=1[CH3:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 178418443HCID 178418443, compound

Product 1

HCID 574330783-(4-Bromo-3-methyl-phenyl)-pentan-3-olYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 4-liter SVL reactor equipped with a magnetic stirrer, a thermometer and a dropping funnel, introduce under nitrogen 198.7 g (0.867 mol) of methyl 4-bromo-3-methylbenzoate in solution in 1 liter of tetrahydrofuran. Cool the mixture to −5° C. with the aid of a bath of ice and sodium chloride. Add 636 cm3 of a 3M solution of ethylmagnesium bromide in diethyl ether, then allow the reaction temperature to increase to ambient temperature. After four hours of reaction, hydrolyze the reaction mixture with 2 liters of a 1 N hydrochloric acid solution. After decanting and separation, extract the aqueous phase with 0.5 liter of ethyl acetate. Wash the combined organic phases with 0.4 liter of water (3×). After drying over sodium sulfate, the product obtained after evaporation of the solvents is purified by chromatography on silica gel (heptane/ethyl acetate=95/5). This gives 150.2 g of 3-(4-bromo-3-methylphenyl)pentan-3-ol in the form of a colorless oil (Yield=67%)

Workup

  1. customIn a 4-liter SVL reactor equipped with a magnetic stirrer
  2. customAfter four hours of reaction
  3. customAfter decanting
  4. customseparation
  5. extractionextract the aqueous phase with 0.5 liter of ethyl acetate
  6. washWash the combined organic phases with 0.4 liter of water (3×)
  7. dry with materialAfter drying over sodium sulfate
  8. customthe product obtained
  9. customafter evaporation of the solvents
  10. customis purified by chromatography on silica gel (heptane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-66579ddd12474f3fa50d4388a14bfde3
Source dataset
uspto-grants-2010_02
Patent number
US07659421B2

Reaction notes

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