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

HRID 1798059Notes

Reaction equation

HRID 1798059 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.CCOC(C)=O>[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 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-bis-methoxymethoxy-6-methoxymethyl-benzaldehyde (3.93 g, 14.45 mmol) in THF (30 mL) was added 6 N HCl (10 mL). The mixture was stirred at room temperature for 20 hours then diluted with EtOAc (200 mL). The mixture was washed with brine, dried and concentrated to give 2,4-dihydroxy-6-methoxymethyl-benzaldehyde (2.62 g, 100%). 1H NMR (400 MHz, CDCl3δ 12.40 (s, 1H), 10.10 (s, 1H), 6.41 (s, 1H), 6.30 (s, 1H), 5.60 (s, 1H), 4.61 (s, 2H), 3.40 (s, 3H).

Workup

  1. washThe mixture was washed with brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-38a82620bfd6499eaee3241cfee20708
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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