2-Hydroxy-4-Methoxybenzaldehyde → HCID 57978446, compound

HRID 1866210Notes

Reaction equation

HRID 1866210 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([OH:11])[CH:4]=1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17]Cl.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])[CH:4]=1

Participants

5

Reactant 3

HCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531Diisopropylethylamine

Product 1

HCID 57978446HCID 57978446, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-methoxy-2-hydroxybenzaldehyde (6.5 g, 40 mmol), MEM-chloride (10.0 g, 80 mmol) and diisopropylethylamine (21 mL, 120 mmol) in dichloromethane (200 mL) was stirred at 25° C. for 14 h. The reaction mixture was concentrated to a small volume, diluted with diethyl ether (200 mL) and filtered through a short path of silica gel. The filtrate was concentrated to give crude 4-methoxy-2-(methoxyethoxy)methoxy-benzaldehyde which was pure enough for use in the next step.

Workup

  1. concentrationThe reaction mixture was concentrated to a small volume
  2. additiondiluted with diethyl ether (200 mL)
  3. filtrationfiltered through a short path of silica gel
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ee2f415db8ef4999b66277fdd9e703ce
Source dataset
uspto-grants-2009_12
Patent number
US07629372B2

Reaction notes

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