Acetic acid 2-(2-ethoxy-naphthalen-1-yl)-2-oxo-ethyl ester → 1-(2-Ethoxy-naphthalen-1-yl)-2-hydroxy-ethanone

HRID 33566Notes

Reaction equation

HRID 33566 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14](=[O:20])[CH2:15][O:16]C(=O)C)[CH3:2]>Cl>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14](=[O:20])[CH2:15][OH:16])[CH3:2]

Participants

3

Reactant 1

HCID 59796828Acetic acid 2-(2-ethoxy-naphthalen-1-yl)-2-oxo-ethyl ester

Product 1

HCID 597968821-(2-Ethoxy-naphthalen-1-yl)-2-hydroxy-ethanoneYield 71.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of acetic acid 2-(2-ethoxy-naphthalen-1-yl)-2-oxo-ethyl ester (6.1 g), industrial methylated spirits (40 mL) and 1M hydrochloric acid (30 mL) was heated at reflux for 2 hours. After cooling to room temperature, the solvent was removed under reduced pressure to afford a brown oil. Purification by column chromatography, eluting with 30% to 40% ethyl acetate in cyclohexane, afforded 1-(2-ethoxy-naphthalen-1-yl)-2-hydroxy-ethanone (3.7 g, 71%) as an orange solid. 1H NMR (CDCl3): 1.4 (3H, t, J=7.0 Hz), 3.5 (1H, t, J=5.1 Hz), 4.2 (2H, q, J=7.0 Hz), 4.75 (2H, d, J=5.1 Hz), 7.25 (1H, d, J=9.0 Hz), 7.35 (1H, m), 7.5 (1H, m), 7.75 (1H, d, J=8.1 Hz), 7.85 (1H, d, J=7.8 Hz), 7.9 (1H, d, J=9.0 Hz).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solvent was removed under reduced pressure
  3. customto afford a brown oil
  4. customPurification by column chromatography
  5. washeluting with 30% to 40% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-71575545f8664133806a2a62907b0dcf
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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