Methyl chloroformate → 2-Methyl-1-naphthol

HRID 37683

Reaktionsgleichung

Reaktionsgleichung von HRID 37683
C1(O)C2C(=CC=CC=2)C=CC=1.[OH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[C:23](O)=O.ClC(OC)=O.[BH4-].[Na+]>C1COCC1.C(N(CC)CC)C>[CH3:23][C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1[OH:12]

Komponenten

7

Edukt 4

HCID 6586Methyl chloroformateHCID 68441-Hydroxy-2-naphthoic acid2×HCID 70051-NaphtholHCID 4311764Sodium borohydride

Produkt 1

HCID 240552-Methyl-1-naphtholAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

1-naphthol (5) was heated with twice its weight of KHCO3 at 200° C. for 5 hours (stainless steel bomb) whereby 1-hydroxy-2-naphthoic acid (9) was obtained in a yield of 60%. 1-Hydroxy-2-naphthoic acid (9) was treated with methyl chloroformate and triethylamine in THF, followed by sodium borohydride reduction, whereby 2-methyl-naphthol (I) was produced in a yield of 80%.

Aufarbeitung

  1. customwas obtained in a yield of 60%

Quellen und Nachweise

ORD-Eintrag
ord-9268980dbcd94c068c537f2d13247f9b
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420362

Verknüpfte Notizen

Wird geladen…