Hydrochloric Acid → 1-(2,6-dihydroxyphenyl)-propan-1-one

HRID 527524Notes

Reaction equation

HRID 527524 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:18])[CH2:16][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:18])[CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22614991HCID 22614991, compound2×

Product 1

HCID 116223911-(2,6-dihydroxyphenyl)-propan-1-oneYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-1-propanone (Intermediate 27, 1.7 g) was dissolved in methanol (50.0 ml) and an aqueous solution of HCl (26.7 ml, 53.5 mmol of a 2M aqueous solution) was added. The reaction mixture was refluxed for 2 hours. 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 (1.11 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  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-4384d7b35b4c45d1a8745f02dca65394
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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