Hydrochloric Acid → 5-Methoxy-2-methylbenzene-1,3-diol

HRID 2272778Notes

Reaction equation

HRID 2272778 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:14]COC)[C:6]([CH3:13])=[C:7]([O:9]COC)[CH:8]=1.Cl.O>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:14])[C:6]([CH3:13])=[C:7]([OH:9])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 251387855-Methoxy-1,3-bis(methoxymethoxy)-2-methylbenzene

Product 1

HCID 2387695-Methoxy-2-methylbenzene-1,3-diolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 9 (314 mg, 1.30 mmol) in MeOH (10.8 mL) at room temperature was treated dropwise with 3 M HCl (3.46 mL, 10.3 mmol), then heated to reflux for one hour. Water (11 mL) was added and the solution was extracted with EtOAc (3×15 mL). Combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated to afford 10 as a red amorphous solid (177 mg, 99%): 1H NMR (CDCl3, 500 MHz) δ 8.17 (s, 1H), 6.09 (d, J=1.6 Hz, 1H), 6.04 (s, 1H), 3.67 (d, J=9.9 Hz, 3H), 2.08 (d, J=4.1 Hz, 3H); 13C NMR (CDCl3, 125 MHz) δ 160.3, 157.8, 155.4, 108.4, 93.9, 93.8, 55.0, 7.0; IR (film) νmax 3445, 2924, 2853, 2359, 2332, 1653, 1636, 1456, 1080, 1022, 798, 669 cm−1; HRMS (ESI+) m/z: [2M+H]+ calcd for C8H10O3, 309.1338 found, 309.1332.

Workup

  1. temperatureheated
  2. temperatureto reflux for one hour
  3. extractionthe solution was extracted with EtOAc (3×15 mL)
  4. washCombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e41fbcb6eb5f4c57b85e2ff2030595a2
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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