2-Methylresorcinol → HCID 20334274, compound

HRID 1706716Notes

Reaction equation

HRID 1706716 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].[CH3:10][C:11]([CH2:16][CH2:17][CH3:18])=[CH:12][C:13](Cl)=[O:14]>>[OH:4][C:3]1[C:2]([CH3:1])=[C:8]2[C:7]([C:13](=[O:14])[CH2:12][C:11]([CH3:10])([CH2:16][CH2:17][CH3:18])[O:9]2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 118432-MethylresorcinolHCID 54328643HCID 54328643, compound

Product 1

HCID 20334274HCID 20334274, compoundYield 69.7%

Conditions

Temperature
60 °C

Procedure

To the mixture of 19.8 g. of 2-methyl resorcinol and 50 ml of boron trifluoride-ethyl ether complex were added dropwise 30 g. of 3-methyl-2-hexenoyl chloride with stirring at 45° C. for about 30 minutes. After stirring for 2 hours at about 60° C., the reaction mixture was poured into ice water, and extracted with ether. After washing with water, the ether layer was extracted with 5% aqueous solution of sodium hydroxide. After acidification with hydrochloric acid, the aqueous solution of sodium hydroxide was extracted with ether. The ether layer was washed with water, and dried over magnesium sulfate. The product was purified by subjecting to column chromatography filled with silica gel to obtain 26.1 g. (yield: 69.7%) of the subject compound as oily product.

Workup

  1. additionTo the mixture of 19.8 g
  2. extractionextracted with ether
  3. washAfter washing with water
  4. extractionthe ether layer was extracted with 5% aqueous solution of sodium hydroxide
  5. extractionAfter acidification with hydrochloric acid, the aqueous solution of sodium hydroxide was extracted with ether
  6. washThe ether layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customThe product was purified
  9. additionfilled with silica gel
  10. customto obtain 26.1 g

Sources & evidence

ORD record
ord-da4e138741214e52a375c126d80e6fe9
Source dataset
uspto-grants-1980_06
Patent number
US04208426

Reaction notes

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