Dicyclohexylamine → 4-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoyl chloride
Reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[C:16][C:17]3[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:42])=O>ClCCl>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14][C:15]#[C:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([Cl:42])=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2.9 g (8.3 mmol) of 4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoic acid and 100 ml of dichloromethane are introduced into a round-bottomed flask under a stream of nitrogen and 2.4 ml (12.1 mmol) of dicyclohexylamine are added dropwise. The mixture is stirred at room temperature for one hour, 1.2 ml (11.7 mmol) of thionyl chloride are added dropwise and the mixture is stirred for one hour. The reaction medium is evaporated to dryness, the residue is taken up in ethyl ether, the dicyclohexylamine salt is filtered off and the filtrate is evaporated. 3 g (100%) of the crude acid chloride are collected, which product will be used in its current state for the rest of the synthesis.
Workup
- additionare added dropwise
- stirringthe mixture is stirred for one hour
- customThe reaction medium is evaporated to dryness
- filtrationthe dicyclohexylamine salt is filtered off
- customthe filtrate is evaporated
- custom3 g (100%) of the crude acid chloride are collected
- customwhich product will be used in its current state for the rest of the synthesis
Sources & evidence
- ORD record
- ord-cc5fd2de154a4951a6e2947e259400f2
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313162B1
Reaction notes
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