Hydrochloric Acid → Acetyl chloride

HRID 1156703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1156703
[ClH:1].C(N[CH2:7][C:8](C1C=CC(O)=C(O)C=1)=[O:9])(C)(C)C.C[O-].[Na+].[C:21]([Cl:31])(=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.C(NCC(CNCCCC)=O)CCC.Cl.Cl.[OH:48][C:49]1[CH:50]=[C:51]([CH:60]=[CH:61][C:62]=1[O:63][C:64](=[O:73])[C:65]1[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][CH:66]=1)[CH:52]([OH:59])[CH2:53][NH:54][C:55]([CH3:58])([CH3:57])[CH3:56]>CN(C)C=O>[C:21]([Cl:31])(=[O:30])[CH3:22].[ClH:1].[C:21]([O:59][CH:52]([CH2:53][NH:54][C:55]([CH3:58])([CH3:57])[CH3:56])[C:51]1[CH:60]=[CH:61][C:62]([O:63][C:64](=[O:73])[C:65]2[CH:66]=[CH:67][C:68]([O:71][CH3:72])=[CH:69][CH:70]=2)=[C:49]([OH:48])[CH:50]=1)(=[O:30])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.[ClH:31].[C:8]([O:59][CH:52]([CH2:53][NH:54][C:55]([CH3:58])([CH3:57])[CH3:56])[C:51]1[CH:60]=[CH:61][C:62]([O:63][C:64](=[O:73])[C:65]2[CH:66]=[CH:67][C:68]([O:71][CH3:72])=[CH:69][CH:70]=2)=[C:49]([OH:48])[CH:50]=1)(=[O:9])[CH3:7]

Komponenten

10

Edukt 6

HCID 313Hydrochloric Acid3×HCID 7477p-Anisoyl chloride2×HCID 30157041-(3,4-Dihydroxyphenyl)-2-((1,1-dimethylethyl)amino)ethan-1-one hydrochlorideHCID 10942334Sodium MethoxideHCID 122950773-Hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochlorideHCID 57304251HCID 57304251, Verbindung

Produkt 3

HCID 6367Acetyl chlorideHCID 20535421HCID 20535421, VerbindungHCID 86736300HCID 86736300, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Using a procedure similar to that described above in Example 58A, 26 g. of 3,4-dihydroxyphenyl tert-butylaminomethyl ketone hydrochloride was reacted with 16 g. of sodium methoxide in N,N-dimethylformamide under an atmosphere of nitrogen and then 17 g. of p-anisoyl chloride was added to produce 35 g. of 3-hydroxy-4-(p-anisoyloxy)phenyl test-butylaminomethyl ketone, m.p. 170°-175° C. (dec.)(uncorr.), which was converted to 28 g. of the hydrochloride, m.p. 235° C. (dec.)(uncorr.). This hydrochloride (26 g.) was catalytically hydrogenated, using a procedure similar to that described above in Example 30B, to yield 19 g. of 3-hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)-benzyl alcohol hydrochloride as a white crystalline solid which melted at 211°-213° C. (dec.)(uncorr.). By interacting this hydrochloride with p-anisoyl chloride and with acetyl chloride, there are obtained 3-hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl p-anisate hydrochloride and 3-hydroxy-4-(p-anisoyloxy)-alpha-(tert-butylaminomethyl)benzyl acetate hydrochloride, respectively.

Aufarbeitung

  1. customto produce 35 g
  2. customto yield 19 g

Quellen und Nachweise

ORD-Eintrag
ord-71901ce55d844a76b7caeb3ad95914cc
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04336400

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