Orcinol → 7-Hydroxy-2,2,5-trimethyl-2,3-dihydro-4H-1-benzopyran-4-one

HRID 1959150Notes

Reaction equation

HRID 1959150 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.[CH3:10][C:11]([CH3:16])=[CH:12][C:13](O)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-].P(Cl)(Cl)(Cl)=O>>[OH:8][C:6]1[CH:5]=[C:4]2[C:3]([C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:10])[O:9]2)=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 4

HCID 10436OrcinolHCID 109313-Methyl-2-butenoic acidHCID 24813Phosphorus oxychlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27279647-Hydroxy-2,2,5-trimethyl-2,3-dihydro-4H-1-benzopyran-4-one

Procedure

Anhydrous 5-methylbenzene-1,3-diol (3.678 g), 3,3-dimethylacrylic acid (3.3 mL) and aluminum chloride (14.76 g) were added to phosphoryl chloride (45 mL) and the mixture was shaken at room temperature for 6 hours. The reaction solution was poured into ice, and the precipitates were filtered, washed with water and dried. The precipitates were purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=25/1) to give the titled compound (3.8 g) as a colorless powder.

Workup

  1. additionThe reaction solution was poured into ice
  2. filtrationthe precipitates were filtered
  3. washwashed with water
  4. customdried
  5. customThe precipitates were purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=25/1)

Sources & evidence

ORD record
ord-971046fbcd4249d2ab2ebfbd94d15645
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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