Acetic Acid → 5-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 1242936Notes

Reaction equation

HRID 1242936 reaction equation
C(C1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2)#N.[C:14]([OH:17])(=[O:16])[CH3:15]>Cl>[O:13]=[C:9]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:4]=[C:15]([C:14]([OH:17])=[O:16])[CH:12]=[CH:11][C:10]1=2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 108991325-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

6-Cyano-1-tetralone (1.30 g, 7.59 mmol) synthesized by a known literature method (Synthetic Communications, 23(21), 2965 (1993)) was dissolved in a mixed solution of concentrated hydrochloric acid (10 ml) and acetic acid (20 ml), which was stirred at 120° C. for 16 hours. The reaction mixture was concentrated. Ethyl acetate and water were added to the residue, and extraction was conducted. The organic layer was washed with water, and concentrated. The residue was washed with ethyl acetate-n-hexane (1:1), to give 5-oxo-5,6,7,8-tetrahydro-2-naphthalenecarboxylic acid (1.10 g) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionEthyl acetate and water were added to the residue, and extraction
  3. washThe organic layer was washed with water
  4. concentrationconcentrated
  5. washThe residue was washed with ethyl acetate-n-hexane (1:1)

Sources & evidence

ORD record
ord-411efc7dcd0d446c9a1e880c2cb488e9
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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