Catechol → HCID 12637527, compound

HRID 434524Notes

Reaction equation

HRID 434524 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH2:9]([C:11]1([O:15][CH2:14]1)[CH2:12]Cl)[CH3:10].[OH-].[Na+]>O>[OH:15][CH2:14][C:11]1([CH2:9][CH3:10])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2][CH2:12]1

Participants

5

Reactant 3

HCID 289CatecholHCID 14798Sodium HydroxideHCID 108443802-(Chloromethyl)-1,2-epoxybutane

Product 1

HCID 12637527HCID 12637527, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A stirred mixture of catechol (14.0 g), 2-ethyl-epichlorohydrin (15.3 g), sodium hydroxide (5.1 g) and water (50 ml) was heated at 90° under an atmosphere of nitrogen for 4 hours. On cooling water was added and the product was extracted with methylene chloride. The combined extracts were washed with 2 N aqueous sodium hydroxide solution, water and brine, dried and evaporated to leave an oil (10.8 g); IR νmax 3650-3200, 3000-2850 cm-1.

Workup

  1. temperaturewas heated at 90° under an atmosphere of nitrogen for 4 hours
  2. additionwas added
  3. extractionthe product was extracted with methylene chloride
  4. washThe combined extracts were washed with 2 N aqueous sodium hydroxide solution, water and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-6e3e690eb2704888bd7711d4cbf79ea0
Source dataset
uspto-grants-1983_08
Patent number
US04397860

Reaction notes

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