Dicyclohexylamine → 4-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzoic acid chloride

HRID 618501

Reaktionsgleichung

Reaktionsgleichung von HRID 618501
[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:52])=O>ClCCl>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:29]=[CH:28][C:24]([C:25]([Cl:52])=[O:26])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Komponenten

5

Edukt 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 216241CD 2665

Produkt 1

HCID 1317213724-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzoic acid chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10 g (20.6 mmol) of 4-[7-(1-adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzoic acid and 100 ml of dichloromethane were introduced into a round-bottomed flask and 4.3 ml (21.6 mmol) of dicyclohexylamine were added dropwise. The reaction mixture was stirred at room temperature for one hour and 2.2 ml (21.6 mmol) of thionyl chloride were added dropwise. The reaction mixture was stirred for one hour and was evaporated to dryness, the residue was taken up in ethyl ether, the dicyclohexylamine salt was filtered off and the filtrate was evaporated. 10.4 g (100%) of the crude acid chloride were collected, which acid chloride was used as is in the synthesis to follow.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for one hour
  2. customwas evaporated to dryness
  3. filtrationthe dicyclohexylamine salt was filtered off
  4. customthe filtrate was evaporated
  5. custom10.4 g (100%) of the crude acid chloride were collected
  6. customas is in the synthesis

Quellen und Nachweise

ORD-Eintrag
ord-243fee5c3bd549d88bb5bc52367f9057
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952382

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