2,4-Dihydroxybenzaldehyde → 2-Hydroxy-4-(methoxymethoxy)benzaldehyde

HRID 1044437Notes

Reaction equation

HRID 1044437 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[CH2:17](Cl)[O:18][CH3:19]>CC(C)=O>[OH:7][C:8]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium Carbonate

Product 1

HCID 27550732-Hydroxy-4-(methoxymethoxy)benzaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Oven-dried potassium carbonate (1.38 g, 10 mmol) was added to an ice cooled solution of 2,4-dihydroxy-benzaldehyde (1.38 g, 10 mmol) in 10 mL of acetone. MOMCl (1.54 mL, 20 mmol) was added drop-wise and the mixture was stirred at 0° C. for one hour, after which it was gradually allowed to come to RT. The reaction was further stirred for 24 hours at RT and then poured into ice water with vigorous stirring. A Buff colored solid precipitated. The solid was filtered, dried and recrystallized from MeOH:DCM (ca. 30:5 mL) to obtain 1.31 g (72%) of white solid: mp 52-53° C. [Lit.(65) 50-51° C.]; TLC Rf0.43 in hexanes:EtOAc (2:1), 1H NMR (400 MHz, CDCl3) δ 11.38 (s, 1H, OH), 9.74 (s, 1H, CHO), 7.46-7.44 (d, 1H, J=8.4 Hz, Ar—H6), 6.66-6.64 (dd, 1H, 2J=8.4 Hz, 3J=2 Hz, Ar—H5), 6.60 (d, 1H, 3J=2 Hz), 5.24 (s, 2H, O—CH2—O), 3.48 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3) δ 194.8, 164.5, 164.4, 135.6, 116.2, 109.3, 103.6, 94.3, 56.7.

Workup

  1. customto come to RT
  2. stirringThe reaction was further stirred for 24 hours at RT
  3. customprecipitated
  4. filtrationThe solid was filtered
  5. customdried
  6. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-c6f0f887643e4364bd67dffafa686218
Source dataset
uspto-grants-2013_10
Patent number
US08563599B2

Reaction notes

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