Hydrochloric Acid → 1-(2,6-Dihydroxyphenyl)-2-methyl-1-propanone

HRID 527532Notes

Reaction equation

HRID 527532 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]COC)[C:6]=1[C:15](=[O:19])[CH:16]([CH3:18])[CH3:17].Cl>CO>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[C:15](=[O:19])[CH:16]([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 679585761-(2,6-Bis{[(methyloxy)methyl]oxy}phenyl)-2-methyl-1-propanone2×

Product 1

HCID 134833211-(2,6-Dihydroxyphenyl)-2-methyl-1-propanoneYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-2-methyl-1-propanone (Intermediate 36, 1.58 g, 5.89 mmol) was dissolved in methanol (40.0 ml) and an aqueous solution of HCl (23.6 mL of a 2M aqueous solution, 47.1 mmol) was added. The reaction mixture was refluxed for 1 hour. After quenching with water, the reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated to afford the title compound (916 mg).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customAfter quenching with water
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialThe gathered organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-cd3b80daa5fa4eb7989f5606870afe0e
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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