1-Naphthoic acid → HCID 15887808, compound

HRID 561334Notes

Reaction equation

HRID 561334 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-2c73ab895fb74018a1b75eb51f6c6443
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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