Water → 2-(Methoxymethoxy)-4-(phenylmethoxy)benzaldehyde

HRID 1982768Notes

Reaction equation

HRID 1982768 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][O:11][CH2:12]Cl.[CH2:14]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[C:24]([OH:30])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>O1CCCC1>[CH2:14]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[C:24]([O:30][CH2:10][O:11][CH3:12])[CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl Ether2×HCID 81531Diisopropylethylamine2×HCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Product 1

HCID 178620602-(Methoxymethoxy)-4-(phenylmethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-diisopropylethylamine (1.98 ml) and chloromethyl methyl ether (0.76 ml) were added to a solution of 4-benzyloxy-2-hydroxybenzaldehyde (2071 mg) in tetrahydrofuran (30 ml), and this reaction mixture was stirred and heated under reflux for 19 hours. N,N-diisopropylethylamine (2.7 ml) and chloromethyl methyl ether (1.04 ml) were further added, and the resulting mixture was stirred and heated under reflux for another 10 hours. After water was added, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate, then filtered through silica gel and alumina. The filtrate was concentrated under reduced pressure to give the title compound (2470 mg). This compound was used in the following reaction without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 19 hours
  3. stirringthe resulting mixture was stirred
  4. temperatureheated
  5. temperatureunder reflux for another 10 hours
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. washwashed with a saturated aqueous ammonium chloride solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered through silica gel and alumina
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e9966dfaa9ac44e9b14649a136b89dc0
Source dataset
uspto-grants-2009_06
Patent number
US07541332B2

Reaction notes

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