Methanol → 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester

HRID 558028

Reaction equation

HRID 558028 reaction equation
[CH3:1]O.S(=O)(=O)(O)O.[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH:19]([CH3:23])[C:20]([OH:22])=[O:21])[CH:13]=[CH:12]2>CCCCCC>[CH3:1][O:21][C:20](=[O:22])[CH:19]([C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[CH:15]=1)[CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 162920Desmethylnaproxen

Product 1

HCID 5988972-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl esterYield 89.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of methanol (2100 ml) and sulphuric acid (84 ml) was added 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid (420 grams). The reaction mixture was refluxed for 6 Hours. Methanol (1000 ml) was distilled, and the cooled reaction mass was poured onto ice water to yield crude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester which was filtered, dried and recrystallized using a mixture of ethyl acetate:hexane to yield pure product (400 grams, 89.5% yield) as a white fluffy powder with a melting point of 89.5-92° C. The pure product was characterized using 1H NMR spectroscopy in CDCl3 δ 1.60 (d, 3H, CH3), 3.70 (s, 3H, Ester), 3.88 (q, 1H, CH), 5.36 (bs, 1H, OH), 7.08 (m, 2H, Ar), 7.48 (m, 1H, Ar), 7.65 (m, 3H, Ar).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 Hours
  2. distillationMethanol (1000 ml) was distilled
  3. customthe cooled reaction mass
  4. additionwas poured onto ice water
  5. customto yield crude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester which
  6. filtrationwas filtered
  7. customdried
  8. customrecrystallized
  9. additiona mixture of ethyl acetate

Sources & evidence

ORD record
ord-cf7cd53e39bd4b0b8a76f2166fc27231
Source dataset
uspto-grants-2011_11
Patent number
US08062653B2

Linked notes

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