Hydrochloric Acid → 5-Hydroxy-2-Methoxybenzaldehyde

HRID 1473902Notes

Reaction equation

HRID 1473902 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11]COC)=[CH:7][C:4]=1[CH:5]=[O:6].Cl.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[OH:11][C:8]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:7]=1)[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23439987HCID 23439987, compound

Product 1

HCID 3583415-Hydroxy-2-MethoxybenzaldehydeYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-methoxy-5-(methoxymethoxy)benzaldehyde (33.5 g, 0.17 mol, 1 eq.) in THF (150 mL) was added HCl (3 N, 250 mL, 4.4 eq.). The reaction was stirred at 50° C. for 1 h, cooled to rt, and diluted with water (500 mL). The mixture was neutralized to pH 7-8 with solid K2CO3. The pale yellow solid was collected, washed with water, and dried to give 5-hydroxy-2-methoxybenzaldehyde (17.9 g, 74.6%) as a pale yellow solid. 1H NMR (400 MHz; DMSO) δ=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H). LRMS (M+H+) m/z 154.0.

Workup

  1. temperaturecooled to rt
  2. customThe pale yellow solid was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-79756edd0374408daa2c1c89e7a34360
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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