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

HRID 618501

Reaction equation

HRID 618501 reaction equation
[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

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 216241CD 2665

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-243fee5c3bd549d88bb5bc52367f9057
Source dataset
uspto-grants-1999_09
Patent number
US05952382

Linked notes

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