Hydrochloric Acid → Ethyl 2-naphthylacetate

HRID 989521Notes

Reaction equation

HRID 989521 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14].[CH2:16](O)[CH3:17]>>[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 113932-Naphthaleneacetic acid

Product 1

HCID 256821Ethyl 2-naphthylacetateYield 99%

Procedure

A steady stream of anhydrous hydrochloric acid was bubbled subsurface into a solution of 2-naphthylacetic acid (251.38 grams, 1.35 mol) dissolved in ethanol (1760 mL) over a period of 10 minutes. The resulting solution was stirred at ambient temperature until complete as determined by hplc (2 hours). The reaction mixture was concentrated to dryness. The resulting oil was dissolved in ethyl acetate (200 mL) and filtered through silica gel (300 grams) eluting the product with ethyl acetate (1400 mL). The filtrate was concentrated to give 286.33 grams (99%) of ethyl 2-(2-naphthyl)acetate as a colorless oil. MS (FIA) m/z 215.3 [(M+H)+]. 1H nmr (DMSO-d6): δ 1.15-1.24 (t, 3H), 3.81-3.86 (d, 2H), 4.07-4.15 (q, 2H), 7.41-7.55 (m, 3H), 7.80-7.92 (m, 4H).

Workup

  1. customas determined by hplc (2 hours)
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionThe resulting oil was dissolved in ethyl acetate (200 mL)
  4. filtrationfiltered through silica gel (300 grams)
  5. washeluting the product with ethyl acetate (1400 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3ec584198dbe4038b72caa6c9ba30bd1
Source dataset
uspto-grants-2003_10
Patent number
US06639076B1

Reaction notes

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