Dicyclohexylamine → 3-(1-Adamantyl)-4-methoxyethoxymethoxybenzoyl chloride

HRID 1957694Notes

Reaction equation

HRID 1957694 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[C:14](O)=[O:15])[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:42])=O>ClCCl>[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])[C:14]([Cl:42])=[O:15])[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 153780913-(1-Adamantyl)-4-methoxyethoxymethoxybenzoic acid

Product 1

HCID 572331023-(1-Adamantyl)-4-methoxyethoxymethoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3 g (8.3 mmol) of 3-(1-adamantyl)-4-methoxyethoxymethoxybenzoic acid in 50 ml of anhydrous dichloromethane was introduced into a round-bottomed flask, 1.7 ml (8.3 mmol) of dicyclohexylamine was added and the mixture was stirred for one hour. 600 μl (8.3 mmol) of thionyl chloride were then added and the mixture was stirred for one hour. It was evaporated to dryness, the residue was taken up in anhydrous ethyl ether, the dicyclohexylamine salt was filtered off and the filtrate was evaporated. 3.3 g (100%) of the crude acid chloride, which was used without further purification for the remainder of the synthesis, were recovered.

Workup

  1. stirringthe mixture was stirred for one hour
  2. customIt was evaporated to dryness
  3. filtrationthe dicyclohexylamine salt was filtered off
  4. customthe filtrate was evaporated
  5. custom3.3 g (100%) of the crude acid chloride, which was used without further purification for the remainder of the synthesis
  6. customwere recovered

Sources & evidence

ORD record
ord-135e90d9bb8d48199517bcdca299b407
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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