Triethylamine → HCID 86686943, compound

HRID 1753265Notes

Reaction equation

HRID 1753265 reaction equation
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[C:9](Cl)(=[O:18])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[OH:7][CH:4]1[CH2:5][CH2:6][CH:1]([O:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111621,4-CyclohexanediolHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 86686943HCID 86686943, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,4-cyclohexanediol (20.0 g, 172.4 mmol) was dissolved in dichloromethane (200 mL). Cinnamoyl chloride (7.2 g, 43.1 mmol) dissolved in 50 ml dichloromethane was then slowly added. After 2 h of mixing, triethyl amine (5.3 g, 52 mmol) was added slowly. After 48 h of mixing, the solution was washed three times with dilute HCl (1 M) and two more times with H2O before it was dried over MgSO4 and filtered. The product was then dissolved in methanol which resulted in precipitation of the byproduct. After filteration and evaporating the solvents from the filtrate, the product was a obtained as yellow-orange viscous liquid, which was used without further purification. Yield: 25-40%.

Workup

  1. additionwas then slowly added
  2. additionAfter 2 h of mixing
  3. additionAfter 48 h of mixing
  4. washthe solution was washed three times with dilute HCl (1 M) and two more times with H2O before it
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. dissolutionThe product was then dissolved in methanol which
  8. customresulted in precipitation of the byproduct
  9. customAfter filteration and evaporating the solvents from the filtrate
  10. customa obtained as yellow-orange viscous liquid, which
  11. customwas used without further purification

Sources & evidence

ORD record
ord-3b0b227d67b142e49f287691d1c24c1f
Source dataset
uspto-grants-2015_10
Patent number
US09163114B2

Reaction notes

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