Hydrochloric Acid → 4-Methoxy-2-methylbenzene-1,3-diol

HRID 1511218Notes

Reaction equation

HRID 1511218 reaction equation
C(OC[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14]COCC)[C:7]=1[CH3:19])C.Cl.O>CO>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[C:7]([CH3:19])[C:8]=1[OH:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 251402551,3-Bis(ethoxymethoxy)-4-methoxy-2-methylbenzene

Product 1

HCID 251409964-Methoxy-2-methylbenzene-1,3-diolYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5a (910 mg, 3.37 mmol) in MeOH (28.0 mL) at room temperature was treated dropwise with 3 M HCl (9.00 mL, 26.9 mmol), then heated to reflux for 1 hour. Water (30 mL) was added and the solution was extracted with EtOAc (3×30 mL). Combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 6:1 Hexane:EtOAc) to afford 6a as a red amorphous solid (509 mg, 98%): 1H NMR (Acetone-d6, 500 MHz) 7.68 (s, 1H), 7.24 (s, 1H), 6.60 (d, J=11 Hz, 1H), 6.29 (d, J=11 Hz, 1H), 3.74 (s, 3H), 2.09 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 144.7, 142.1, 139.7, 115.6, 110.2, 108.6, 55.6, 7.6; IR (film) νmax 3583, 2920, 2359, 1616, 1259, 1090, 1020, 798 cm−1.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. extractionthe solution was extracted with EtOAc (3×30 mL)
  4. washCombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography (SiO2, 6:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-0bdfb524054b4973872a09190a7edf5c
Source dataset
uspto-grants-2012_07
Patent number
US08212011B2

Reaction notes

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