Hydrochloric Acid → (E)-ethyl 4-styrylbenzoic acid

HRID 533716Notes

Reaction equation

HRID 533716 reaction equation
[CH3:1][OH:2].[Li+].[OH-:4].Cl.[CH2:6]1[CH2:10]O[CH2:8][CH2:7]1>O>[CH2:7]([C:6]1[CH:10]=[C:8](/[CH:10]=[CH:6]/[C:7]2[CH:8]=[CH:7][CH:6]=[CH:10][CH:8]=2)[CH:7]=[CH:6][C:10]=1[C:1]([OH:4])=[O:2])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 8028Tetrahydrofuran

Product 1

HCID 67246536(E)-ethyl 4-styrylbenzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ester (E)-ethyl 4-styrylbenzoate (600 mg, 2.3 mmol) in THF (5 mL) was added MeOH (2 mL) and a solution of LiOH (360 mg, 10 mmol) in water (25 mL). The reaction was stirred at room temperature and for 4 h. The reaction was acidified with 1 N HCl (10 mL) and isolated (E)-ethyl 4-styrylbenzoic acid (440 mg, 83%) as a white solid; 1H-nmr (400 MHz, CDCl3) δ 8.11 (d, J=8.0 Hz, 2H), 7.75-7.68 (m, 1H), 7.64 (d, J=8.0 Hz, 2H), 7.62-7.56 (m, 2H), 7.52-7.47 (m, 1H), 7.43-7.36 (m, 3H), 6.97 (d, 1H), 6.88 (d, 1H); LCMS (214 nM) 3.22 min (>98%); MS (ESI) m/z=225.1.

Sources & evidence

ORD record
ord-1f33c5de67bb4b4ab9dfb8bb05a7cec6
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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