Dichloromethane → HCID 53728690, compound

HRID 2417341Notes

Reaction equation

HRID 2417341 reaction equation
[CH3:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([C:22](=C)[C:23](O)=O)[CH:19]=[CH:20][CH:21]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.C1(NC2CCCCC2)CCCCC1.S(Cl)(Cl)=[O:41].Cl[CH2:45][Cl:46]>>[CH3:1][C:2]1[C:3]([C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][C:45]([Cl:46])=[O:41])[CH:19]=[CH:20][CH:21]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 22634659HCID 22634659, compound

Product 1

HCID 53728690HCID 53728690, compound

Procedure

3.5 g (10 mmol) of 3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenylacrylic acid and 50 ml of dichloromethane are introduced into a round-bottomed flask and 2 ml (10 mmol) of dicylcohexylamine are added. The mixture is stirred at room temperature for 10 minutes and 729 μl (10 mmol) of thionyl chloride are then introduced with stirring for 15 minutes. 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. 3.7 g (100%) of the crude acid chloride are collected, which will be used in its current state for the rest of the synthesis.

Workup

  1. stirringwith stirring for 15 minutes
  2. customThe reaction medium is evaporated to dryness
  3. filtrationthe dicyclohexylamine salt is filtered off
  4. customthe filtrate is evaporated
  5. custom3.7 g (100%) of the crude acid chloride are collected
  6. customwhich will be used in its current state for the rest of the synthesis

Sources & evidence

ORD record
ord-979d509a23284408a737a1d124089f12
Source dataset
uspto-grants-2004_11
Patent number
US06825360B1

Reaction notes

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