Hydrochloric Acid → HCID 12953784, compound

HRID 1703189Notes

Reaction equation

HRID 1703189 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]2[C:11]([O:13][C:14](=[O:15])[C:2]=12)=[O:12].[CH3:16][CH:17](C(O)=O)C(O)=O.Cl>C(N(CC)CC)C>[O:12]=[C:11]([C:3]1[C:2]([C:14]([OH:13])=[O:15])=[CH:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 487Methylmalonic AcidHCID 69743Naphtho(2,3-c)furan-1,3-dione

Product 1

HCID 12953784HCID 12953784, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2,3-naphthalenedicarboxylic anhydride (35.5 g), methylmalonic acid (25 g) and triethylamine (250 ml) was stirred and refluxed for 8 hr. The cooled reaction mixture was poured onto 10% hydrochloric acid (2 liter) and the aqueous slurry was extracted with chloroform (1.5 liter). The dried (magnesium sulphate) extract was evaporated to dryness to give an oil which was recrystallised from light petroleum (b.p. 60°-80°)/chloroform to give 3-(1'-oxopropyl)naphthalene-2-carboxylic acid (23 g, m.p. 147°).

Workup

  1. temperaturerefluxed for 8 hr
  2. customThe cooled reaction mixture
  3. extractionthe aqueous slurry was extracted with chloroform (1.5 liter)
  4. dry with materialThe dried (magnesium sulphate)
  5. extractionextract
  6. customwas evaporated to dryness
  7. customto give an oil which
  8. customwas recrystallised from light petroleum (b.p. 60°-80°)/chloroform

Sources & evidence

ORD record
ord-b225db8dd68e44ecb6f086f854bbaa4e
Source dataset
uspto-grants-1982_09
Patent number
US04351842

Reaction notes

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