Pyridine → HCID 13886888, compound

HRID 1003942Notes

Reaction equation

HRID 1003942 reaction equation
[OH2:1].[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12].N1[CH:23]=[CH:22]C=CC=1>>[C:11]([O:5][C:4]1[CH:3]=[C:2]([O:10][C:22](=[O:1])[CH3:23])[CH:9]=[C:7]([CH3:8])[CH:6]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 3083941Resorcinol, 5-methyl-, monohydrate

Product 1

HCID 13886888HCID 13886888, compound

Procedure

Orcinol monohydrate (50 g) is dissolved in pyridine (400 ml), and thereto is added acetic anhydride (133 ml), and the mixture is stirred at room temperature for 17 hours. The reaction mixture is concentrated under reduced pressure, and the resulting residue is dissolved in ethyl acetate (500 ml). The mixture is washed successively with 10% hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure to give orcinol diacetate (74 g).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionthe resulting residue is dissolved in ethyl acetate (500 ml)
  3. washThe mixture is washed successively with 10% hydrochloric acid, water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-426f1607c29f43dd83cbd3ba631532f9
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Reaction notes

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