Dicyclohexylamine → 3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyl chloride

HRID 2268204Notes

Reaction equation

HRID 2268204 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]=[CH:15][C:16](O)=[O:17])[CH:5]=[CH:4][C:3]1=2.C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:35])=O>ClCCl>[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]=[CH:15][C:16]([Cl:35])=[O:17])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 702132933-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acrylic acid

Product 1

HCID 734315563-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.6 g (10 mmol) of 3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acrylic acid in 50 ml of anhydrous dichloromethane is introduced into a round-bottomed flask, 2 ml (10 mmol) of dicyclohexylamine are added and the mixture is stirred for one hour. 800 μl (10 mmol) of thionyl chloride are then added and the mixture is stirred for one hour. The mixture is evaporated to dryness, the residue is taken up in anhydrous ethyl ether, the dicyclohexylamine salt is filtered off and the filtrate is evaporated. 2.8 g (100%) of the crude acid chloride are collected, which product will be used subsequently without further purification.

Workup

  1. stirringthe mixture is stirred for one hour
  2. customThe mixture is evaporated to dryness
  3. filtrationthe dicyclohexylamine salt is filtered off
  4. customthe filtrate is evaporated
  5. custom2.8 g (100%) of the crude acid chloride are collected
  6. customwhich product will be used subsequently without further purification

Sources & evidence

ORD record
ord-1a7675620ccf44ec9cb35a6448c8b761
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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