Hydrochloric Acid → 72985-24-1

HRID 2071102Notes

Reaction equation

HRID 2071102 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:11])=[C:7]([CH:10]=1)[CH:8]=[O:9].OOS([O-])=O.[K+].Cl.[OH2:19].[CH3:20]O>CCOC(C)=O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:11])=[C:7]([CH:10]=1)[C:8]([O:19][CH3:20])=[O:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 595699215-(Hydroxymethyl)-2-methylbenzaldehyde

Product 1

HCID 6850259472985-24-1

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 800 mg of 5-(hydroxymethyl)-2-methylbenzaldehyde in 20 mL of MeOH was added 3.4 g (5.5 mmol) of Oxone. The mixture was stirred at r.t. for 3.75 h and 2 mL of MeOH was added. After 2.5 h, 15 mL of 1N HCl, 45 mL of H2O, and EtOAc were added, and the layers separated. The aqueous layer was extracted, the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 377 mg of methyl 5-(hydroxymethyl)-2-methylbenzoate as a yellow oil with some impurity.

Workup

  1. waitAfter 2.5 h
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash silica gel chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cdd7b3cf699946d29664c3409feb2e37
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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