Hydrochloric Acid → 3-(2-Hydroxymethyl-5-nitrophenylthio)-4-hydroxybenzoic acid

HRID 255930

Reaktionsgleichung

Reaktionsgleichung von HRID 255930
[SH:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[OH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=1I.Cl>CN1CCCC1=O>[OH:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:2]=1[S:1][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:14]=1[OH:13])[C:18]([OH:20])=[O:19]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)HCID 54320749(4-Nitro-2-sulfanylphenyl)methanol

Produkt 1

HCID 212883293-(2-Hydroxymethyl-5-nitrophenylthio)-4-hydroxybenzoic acidAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of 2-mercapto-4-nitrobenzyl alcohol 9.49 g, 18.86 mmoles), 4-hydroxy-3-iodo-benzoic acid (4.67 g, 17.69 mmoles), red cuprous oxide (1.35 g, 9.44 mmoles) and 1-methyl-2-pyrrolidinone (40 ml) was heated under a N2 atmosphere. The mixture became a thick slurry at 90° but at 130° had become a dark red solution. After 1/2 hour at 140° TLC showed that the reaction was finished. The mixture was poured onto 2N HCl (200 ml) and after stirring for a few minutes it was extracted 4× with EtOAc. The EtOAc extracts were washed with water, then extracted 4× with 1N NaOH. The aqueous extracts were washed once with EtOAc then acidified and the resulting solid filtered, washed with water and dried to yield 4.65 g of the title compound.

Aufarbeitung

  1. temperaturewas heated under a N2 atmosphere
  2. customat 90°
  3. customat 130°
  4. extractionwas extracted 4× with EtOAc
  5. washThe EtOAc extracts were washed with water
  6. extractionextracted 4× with 1N NaOH
  7. washThe aqueous extracts were washed once with EtOAc
  8. filtrationthe resulting solid filtered
  9. washwashed with water
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3775e0bba8274821868d943d55700d53
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699917

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