Hydrochloric Acid → 3-Phenylbutyric acid

HRID 593262

Reaction equation

HRID 593262 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]([OH:18])(=[O:17])/[CH:14]=[CH:15]/[CH3:16].Cl>O1CCCC1>[C:7]1([CH:15]([CH3:16])[CH2:14][C:13]([OH:18])=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 637090Crotonic AcidHCID 178418339Butyllithium

Product 1

HCID 207243-Phenylbutyric acidYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

As presented in the following reaction formula, n-butyllithium (n-BuLi; 428 mL, 1.07 mol) was added dropwise at −78° C. to −65° C. to a mixture of bromobenzene (166 g, 1.07 mol) in tetrahydrofuran (THF; 500 mL), followed by stirring at −78° C. for 0.5 hours. Then, (E)-but-2-enoic acid (46 g, 0.53 mol) was added dropwise to the resulting mixture. After the completion of reaction, the mixture was treated with hydrochloric acid so that the pH thereof was adjusted to 1.0, and then extracted twice with 500 mL of dichloromethane (DCM). The combined organic phase was dried and concentrated with magnesium sulfate to give a crude product, which was purified by column chromatography (using 300 g of silica gel (product of Merck Co., Ltd.) to give 3-phenylbutanoic acid (52 g, yield: 60%) as a yellow liquid.

Workup

  1. customAfter the completion of reaction
  2. extractionextracted twice with 500 mL of dichloromethane (DCM)
  3. customThe combined organic phase was dried
  4. concentrationconcentrated with magnesium sulfate
  5. customto give a crude product, which
  6. customwas purified by column chromatography (

Sources & evidence

ORD record
ord-d6fb234995ba403ea1a361ffbcd8273f
Source dataset
uspto-grants-2016_01
Patent number
US09242928B2

Linked notes

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