1-Naphthoic acid → HCID 9860458, compound

HRID 1297488Notes

Reaction equation

HRID 1297488 reaction equation
[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:14]1([S:20][CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:21][S:20][C:14]1[CH:19]=[CH:18][C:17]([C:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[O:13])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 68471-Naphthoic acidHCID 7520Thioanisole

Product 1

HCID 9860458HCID 9860458, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 1-naphthoic acid (10 g, 58.08 mmol), thioanisol (8.19 ml, 69.7 mmol) and polyphosphoric acid (100 g) was heated for 12 hours on water bath at 80° C. Reaction mixture was poured onto ice water and extracted with ethylacetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to give oil, which was crystallized from methanol to give the desired compound.

Workup

  1. customReaction mixture
  2. additionwas poured onto ice water
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give oil, which
  8. customwas crystallized from methanol

Sources & evidence

ORD record
ord-314c0882222649dd94f70751520d99bc
Source dataset
uspto-grants-2007_07
Patent number
US07250446B2

Reaction notes

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