Hydrochloric Acid → 2,4-Dihydroxy-6-methoxymethyl-benzaldehyde

HRID 1798081Notes

Reaction equation

HRID 1798081 reaction equation
COC[O:4][C:5]1[CH:12]=[C:11]([O:13]COC)[CH:10]=[C:9]([CH2:17][O:18][CH3:19])[C:6]=1[CH:7]=[O:8].Cl>C1COCC1.C(OCC)(=O)C>[OH:4][C:5]1[CH:12]=[C:11]([OH:13])[CH:10]=[C:9]([CH2:17][O:18][CH3:19])[C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 582925712,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehyde

Product 1

HCID 582926702,4-Dihydroxy-6-methoxymethyl-benzaldehydeYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2,4-bis-methoxymethoxy-6-methoxymethyl-benzaldehyde (7.21 g, 26.7 mmol) in THF (60 mL) was treated with 6N HCl (20 mL) at room temperature. The resulting mixture was heated to 60° C. for 1 h. The reaction was diluted with ethyl acetate and washed with water. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=1:1) to afford the title compound (4.08 g, 84%). 1H NMR (300 MHz, CD3OD) δ 10.01 (s, 1H), 6.35 (s, 1H), 6.25 (s, 1H), 4.57 (s, 2H), 3.36 (s, 3H), 2.64 (s, 2H).

Workup

  1. washwashed with water
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2e663bd040b447b1a1b89069f28ae32b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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