4-Chlororesorcinol → HCID 86606719, compound

HRID 1714592Notes

Reaction equation

HRID 1714592 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19].[CH2:22]1C[O:25][CH2:24][CH2:23]1>C(Cl)Cl>[C:17]([O:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([O:9][C:24](=[O:25])[CH:23]=[CH2:22])[CH:4]=1)(=[O:20])[CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 17314-ChlororesorcinolHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 86606719HCID 86606719, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chlororesorcinol (86.76 g, 0.60 mol) in anhydrous THF (750 mL) in a 2-liter three neck round bottom flask equipped with dry nitrogen purge, thermo-couple, condenser, and ice-water bath, triethylamine (163.6 g, 1.62 mol) in anhydrous THE (100 mL) was added dropwise in 10 minutes. After 10 minutes, acryloyl chloride (136 g, 1.5 mol) in anhydrous THF (300 mL) was added dropwise in 30-60 minutes (maintain 0-5C of the solution). A precipitate formed immediately, and the mixture was warmed to room temperature and stirred overnight (.about. 15 hrs). The resulting mixture was filtered to remove the solid, and the filtrate was concentrated by rotary evaporation to give a darkly colored viscous liquid. The liquid was dissolved in methylene chloride (200 mL), cooled in an ice bath, washed with 1.0 N sodium hydroxide until pH>10, washed with 1.0 N HCl until pH<2, washed with DI water until pH>5, and dried over anhydrous sodium sulfate. The compound was purified by column chromatography and vacuum concentrated at room temperature to give a pale yellow or colorless liquid.

Workup

  1. custompurge
  2. temperaturemaintain 0-5C of the solution)
  3. customA precipitate formed immediately
  4. custom15 hrs
  5. filtrationThe resulting mixture was filtered
  6. customto remove the solid
  7. concentrationthe filtrate was concentrated by rotary evaporation
  8. customto give a darkly colored viscous liquid
  9. temperaturecooled in an ice bath
  10. washwashed with 1.0 N sodium hydroxide until pH>10
  11. washwashed with 1.0 N HCl until pH<2
  12. washwashed with DI water until pH>5
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe compound was purified by column chromatography and vacuum
  15. concentrationconcentrated at room temperature
  16. customto give a pale yellow or colorless liquid

Sources & evidence

ORD record
ord-29572f9b549a48f7b1a376a05b09263a
Source dataset
uspto-grants-2010_09
Patent number
US07796855B2

Reaction notes

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