1-Naphthoic acid → HCID 15887808, compound

HRID 2225128Notes

Reaction equation

HRID 2225128 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-1a66777e7b2c4464befd2604164917ba
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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