Hydrochloric Acid → 4-Phenethyl-benzoic acid methyl ester

HRID 2421633Notes

Reaction equation

HRID 2421633 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][CH:5]=1.CN1CCCC1=O.[CH2:26]([Mg]Br)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>O.C1COCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 5315090Methyl 4-(((trifluoromethyl)sulfonyl)oxy)benzoateHCID 178419670HCID 178419670, compound

Product 1

HCID 204665344-Phenethyl-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

76A (2.27 g, 8 mmol), N-methylpyrrolidinone (4.4 mL), Fe(acac)3 (140 mg, 0.4 mmol) and dry THF (50 mL) were stirred under nitrogen at room temperature. Phenethylmagnesium bromide (1.0 M in THF, 10 mL) was added by syringe. After stirring for fifteen minutes, HCl (1 M, 20 mL) was slowly added. The mixture was diluted with water and extracted three times with EtOAc. The organic layers were combined, washed with water and then brine, were dried over MgSO4 and were concentrated. Purification was achieved using flash chromatography on SiO2 with hexanes/toluene 50:50. A colourless oil was obtained (1.575 g, 82%). NMR 1H (ppm, CDCl3): 7.94 (d, J3 8.2 Hz, 2H), 7.29-7.13 (m, 7H), 3.89 (s, 3H), 3.01-2.89 (m, 4H).

Workup

  1. extractionextracted three times with EtOAc
  2. washwashed with water
  3. dry with materialbrine, were dried over MgSO4
  4. concentrationwere concentrated
  5. customPurification
  6. customA colourless oil was obtained (1.575 g, 82%)

Sources & evidence

ORD record
ord-8757c6c7718340c2814ce6301b695bb3
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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