Chloromethyl Methyl Ether → HCID 23076398, compound

HRID 1879554Notes

Reaction equation

HRID 1879554 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:19][O:20][CH3:21].CCN(C(C)C)C(C)C>C(Cl)Cl.CCOCC>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH2:19][O:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Product 1

HCID 23076398HCID 23076398, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(benzyloxy)-3-hydroxybenzaldehyde (912 mg, 4 mmol), chloro(methoxy)methane (480 mg, 6 mmol), and DIPEA (1.03 g, 8 mmol) in 20 mL DCM was stirred at rt under Ar atmosphere for 15 h. It was diluted with ether (100 mL) and washed with 0.5 M HCl(2×50 mL) and water (2×80 mL), dried over MgSO4 and concentrated. The crude product was purified with silica chromatography (hexane/EtOAc) to afford 4-(benzyloxy)-3-(methoxymethoxy)benzaldehyde as a clear oil (960 mg, 88%). MS (ESI) m/z 273 (M+H+).

Workup

  1. washwashed with 0.5 M HCl(2×50 mL) and water (2×80 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified with silica chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-91ad9946a3934207bc36c68c4957fab6
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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