3-Hydroxybenzaldehyde → 3-(2-Hydroxy-3-methylbutoxy)benzaldehyde

HRID 74410Notes

Reaction equation

HRID 74410 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[O:10]1[CH:12]([CH:13]([CH3:15])[CH3:14])[CH2:11]1>>[OH:10][CH:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

3

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 1026181,2-Epoxy-3-methylbutane

Product 1

HCID 580277143-(2-Hydroxy-3-methylbutoxy)benzaldehyde

Procedure

A mixture of 3-hydroxybenzaldehyde (11) (1 g, 8.2 mmol) and 1,2-epoxy-3-methylbutane (1.3 mL, 12.3 mmol) was microwaved at 140° C. and 120 psi pressure for 2 h (CEM, Discover). Purification by flash chromatography (0 to 15% Acetone-hexanes gradient) gave 3-(2-hydroxy-3-methylbutoxy)benzaldehyde (135) as a yellow oil. Yield (1.1 g, 65%): 1H NMR (400 MHz, CDCl3) δ 9.98 (s, 1H), 7.41-7.50 (m, 3H), 7.19-7.24 (m, 1H), 4.10 (dd, J=9.4, 3.0 Hz, 1H), 3.97 (dd like t, J=8.4 Hz, 1H), 3.75-3.80 (m, 1H), 2.23 (t, J=4.0 Hz, 1H), 1.86-1.95 (m, 1H), 1.05 (d, J=6.8 Hz, 3H), 1.01 (d, J=6.8 Hz, 3H).

Workup

  1. customwas microwaved at 140° C.
  2. customPurification by flash chromatography (0 to 15% Acetone-hexanes gradient)

Sources & evidence

ORD record
ord-14ef89c5fc0841c99dc611eb555c159f
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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