1-Naphthoic acid → HCID 15887808, compound

HRID 1726513Notes

Reaction equation

HRID 1726513 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:14][S:15](O)(=[O:17])=[O:16]>>[Cl:14][S:15]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[C:1]2[C:11]([OH:13])=[O:12])(=[O:17])=[O:16]

Participants

3

Reactant 2

HCID 68471-Naphthoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 15887808HCID 15887808, compoundYield 80.5%

Procedure

The titled compound was prepared using a modified procedure of Reefschlager et al. (see Reefschlager, J., et al., (2000) EP1038868A2). Naphthalene-1-carboxylic acid (6.56 g, 38.1 mmol) was added in small portions to chlorosulfonic acid (22 g, 12.6 mL, 190 mmol) that was cooled in an ice bath. The reaction was stirred overnight at room temperature. The reaction mixture was poured slowly over ice-water (250 mL) and filtered to afford 45 (8.3 g, 80%) as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 14.0 (s, 1H), 9.11 (d, 1H), 8.80 (d, 1H), 8.08 (d, 1H), 8.00 (d, 1H), 7.56 (m, 2H).

Workup

  1. customThe titled compound was prepared
  2. temperaturewas cooled in an ice bath
  3. filtrationfiltered

Sources & evidence

ORD record
ord-810ba6c24793416f9784759792e0a1e8
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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