Ethanol → Ethyl 3-(3-methoxyphenyl)propanoate

HRID 2044184Notes

Reaction equation

HRID 2044184 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:13][C:14]([OH:16])=[O:15])C(O)=O)[CH:6]=[CH:7][CH:8]=1.[CH2:17](O)[CH3:18]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 5841472-(3-Methoxyphenyl)succinic acid

Product 1

HCID 584318Ethyl 3-(3-methoxyphenyl)propanoateYield 93%

Procedure

A solution of 3-methoxyphenylsuccinic acid (1.500 g, 8.32 mmol) in dry ethanol (15 mL) with a small quantity of DOWEX™ strong acid ion exchange resin was refluxed for 22 h. The reacion mixture was filtered and the solvent evaporated in vacuo to give 1.618 g of ester 25. Yield 93%. 1H NMR (300 MHz, CDCl3) δ ppm: 7.15 (q, J=8.6 Hz, 1H), 6.72 (d, J=7.8 Hz, 1H), 6.65-6.70 (m, 2H), 4.06 (q, J=7.1 Hz, 2H), 3.72 (s, 3H), 2.86 (t, J=7.9 Hz, 2H), 2.54 (t, J=7.9 Hz, 2H), 1.17 (t, J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm: 172.9, 159.7, 142.2, 129.4, 120.6, 114.0, 111.6, 60.4, 55.1, 35.8, 31.0, 14.2; HRMS (EI) m/z: calcd for C12H16O3: 208.1099. found: 208.1104.

Workup

  1. filtrationThe reacion mixture was filtered
  2. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-ae3c29db90a94371bde377cd2c55c955
Source dataset
uspto-grants-2013_11
Patent number
US08586776B2

Reaction notes

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