Sodium Chloride → HCID 59167145, compound

HRID 1443325Notes

Reaction equation

HRID 1443325 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[CH:4][C:3]=1[CH2:12][CH2:13][CH3:14].[Cl-].[Na+].[CH2:17]([Mg]Br)[CH3:18].[Cl-].[NH4+].O1CC[CH2:25][CH2:24]1>C(OCC)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])([CH2:17][CH3:18])[CH2:24][CH3:25])=[CH:4][C:3]=1[CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 20040380HCID 20040380, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 59167145HCID 59167145, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 1-liter three-necked round-bottomed flask, equipped with a magnetic stirrer, a thermometer and a dropping funnel, introduce under nitrogen 47 g (0.18 mol) of methyl 4-bromo-3-propylbenzoate in solution in 250 ml of tetrahydrofuran. Cool the mixture to −5° C. with the aid of a bath of ice and sodium chloride. Add 134 cm3 of a 3M solution of ethylmagnesium bromide in diethyl ether, then allow the reaction temperature to increase without exceeding 5° C. After three hours of reaction, hydrolyze the reaction mixture with 170 cm3 of 2.5M ammonium chloride solution. Extend the organic phase with 200 cm3 of ethyl acetate. Separate the phases and extract the aqueous phase with 2×200 cm3 of methylene chloride. Combine the organic phases, dry them over sodium sulfate and evaporate the solvents. This gives 49.8 g of 3-(4-bromo-3-propylphenyl)pentan-3-ol in the form of colorless oil. (Yield=96%)

Workup

  1. customIn a 1-liter three-necked round-bottomed flask, equipped with a magnetic stirrer
  2. temperatureto increase
  3. customwithout exceeding 5° C
  4. customAfter three hours of reaction
  5. customSeparate the phases
  6. extractionextract the aqueous phase with 2×200 cm3 of methylene chloride
  7. dry with materialdry them over sodium sulfate
  8. customevaporate the solvents

Sources & evidence

ORD record
ord-550de64beb5846979965f9cd50a7e681
Source dataset
uspto-grants-2010_02
Patent number
US07659421B2

Reaction notes

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