3-Ethylphenol → 4-Ethyl-2-hydroxybenzaldehyde

Titanium(IV) chloride (100 mL, 100 mmol, 1M in CH2Cl2) followed by dichloromethyl methyl ether (7.47 mL, 82.5 mmol) was added to a cooled 0° C. solution of 3-ethylphenol (6.11 g, 50 mmol). The reaction mixture was stirred for 45 mins. The mixture was poured into ice and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a bright pink oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave 4-ethyl-2-hydroxy-benzaldehyde (4.9 g, 65%) followed by 2-ethyl-4-hydroxy-benzaldehyde (1.32 g, 18%). A: 1H NMR (400 MHz, CDCl3): δ 1.25 (t, J=7.6 Hz, 3H), 2.67 (d, J=7.6 Hz, 2H), 6.82 (s, 1H), 6.85 (d, J=8.0 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 9.83 (s, 1H), 11.05 (s, 1H). B: 1H NMR (400 MHz, CDCl3): δ 1.27 (t, J=7.6 Hz, 3H), 3.03 (d, J=7.6 Hz, 2H), 6.68 (s, 1H), 6.78 (s, 1H), 6.82 (d, J=8.3 Hz, 1H), 7.77 (t, J=8.3 Hz, 1H), 10.10 (s, 1H).

1. additionThe mixture was poured into ice
2. extractionextracted with EtOAc
3. washThe organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated to a bright pink oil
6. customPurification by flash column chromatography (0% to 10% EtOAc in hexanes)

ORDレコード

ord-d9007ba2b7e54da3aef7ef16b45f57ac

出典データセット

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07622605B2