3-Hydroxybenzaldehyde → 3-(3-methoxypropoxy)benzaldehyde

HRID 1014629Notes

Reaction equation

HRID 1014629 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][O:11][CH2:12][CH2:13][CH2:14]OS(C)(=O)=O>CN(C=O)C>[CH3:10][O:11][CH2:12][CH2:13][CH2:14][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 116939633-Methoxypropyl methanesulfonate

Product 1

HCID 470024603-(3-methoxypropoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alkylation of 3-hydroxybenzaldehyde (11) with methanesulfonic acid 3-methoxypropyl ester following the method used in Example 34 except that the reaction solvent was DMF gave 3-(3-methoxypropoxy)benzaldehyde as a clear oil. Yield (1.32 g, 55%): 1H NMR (400 MHz, CDCl3) δ 9.97 (s, 1H), 7.40-7.47 (m, 3H), 7.15-7.20 (m, 1H), 4.12 (t, J=6.4 Hz, 2H), 3.56 (t, J=6.2 Hz, 2H), 3.35 (s, 3H), 2.05-2.11 (m, 2H).

Sources & evidence

ORD record
ord-7ccfaaf8aad94f42b12a70df7774f275
Source dataset
uspto-grants-2011_07
Patent number
US07982071B2

Reaction notes

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