4-Hydroxybenzaldehyde → 4-(Methoxymethoxy)benzaldehyde
Reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[CH2:12](Cl)[O:13][CH3:14]>CN(C=O)C>[CH3:12][O:13][CH2:14][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To the suspension of NaH (3.25 g, 0.135 mol) in DMF (150 mL) was added 4-hydroxy-benzaldehyde (15.0 g, 0.123 mol) in DMF (10 mL) at 0° C., 5 min. later the reaction mixture became a cake. The heterogeneous mixture was stirred at 0° C. for 30 min. MOMCl (9.96 g, 0.123 mol) was added slowly and the reaction mixture was allowed to warm up to r.t. After stirring at r.t. for 16 h, the volatiles were removed under vacuum. The residue was partitioned between ethyl acetate and water and the water layer was further extracted with ethyl acetate. The combined ethyl acetate extracts were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate-hexanes; 1:4) to afford 4-methoxymethoxy-benzaldehyde (19.0 g, 93%): 1H NMR (300 MHz, CDCl3): δ 9.94 (s, 1 H), 7.88 (m, 2H), 7.18 (m, 2H), 5.29 (s, 2H), 3.53 (s, 2H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:4); Rf=0.86.
Workup
- custom5 min.
- temperatureto warm up to r.t
- stirringAfter stirring at r.t. for 16 h
- customthe volatiles were removed under vacuum
- customThe residue was partitioned between ethyl acetate and water
- extractionthe water layer was further extracted with ethyl acetate
- dry with materialThe combined ethyl acetate extracts were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel (ethyl acetate-hexanes; 1:4)
Sources & evidence
- ORD record
- ord-24278539788540bb95baf67e572fa32c
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514419B2
Reaction notes
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