Water → 5-Methoxy-2-(methoxymethoxy)benzaldehyde

HRID 2213984Notes

Reaction equation

HRID 2213984 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C(N(C(C)C)CC)(C)C.[CH3:21][O:22][CH2:23]Cl.O>C(Cl)Cl>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:21][O:22][CH3:23])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 114355225-Methoxy-2-(methoxymethoxy)benzaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxy-5-methoxybenzaldehyde (10 g, 67.5 mmol) and diisopropylethylamine (14 mL, 80 mmol) in CH2Cl2 (100 mL) was added chloromethyl methyl ether (6.1 mL, 80 mmol) at 0° C., and the mixture was stirred for 15 hours at room temperature. Then, water was added to the solution, the aqueous layer was extracted with CH2Cl2 (100 mL×3). The combined organic layer was washed with saturated aqueous NaCl (100 mL×2), water (100 mL×1), dried over MgSO4, and evaporated to afford the objective compound as a brown oil (11.76 g, 91%), which was used for next reaction without further purification: 1H-NMR (400 MHz, CDCl3) δ3.52 (s, 3H), 3.81 (s, 3H), 5.24 (s, 2H), 7.12 (dd, 1H, J=9.6, 3.2 Hz), 7.18 (d, 1H, J=9.6 Hz), 7.32 (d, 1H, J=3.2 Hz), 10.47 (s, 1H).

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (100 mL×3)
  2. washThe combined organic layer was washed with saturated aqueous NaCl (100 mL×2), water (100 mL×1)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-18870814b0a7487894e7d2f6ef2e8044
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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