4-Hydroxybenzaldehyde → 4-Formylphenyl 4-(heptyloxy)benzoate

Prepared using General Procedure 2: To a stirring solution of 4-(heptyloxy)benzoic acid (1.0 g, 4.23 mmol) in DCM (10 mL) were added DMF (1 drop) and oxalyl chloride (0.47 mL, 5.5 mmol). The reaction mixture was stirred at room temperature for 1 h. Solvent was evaporated under high vacuum. DCM (10 mL) was added and the reaction mixture evaporated again to dryness. The residue was dissolved in DCM (10 mL) then added to a stirring mixture of 4-hydroxy benzaldehyde (0.56 g, 4.6 mmol) and TEA (0.706 mL, 5.07 mmol) in DCM (5 mL) at 0° C. The reaction mixture was allowed to stir at room temperature for 2 h. The reaction mixture was quenched with NaHCO3 (10 mL). The aqueous phase was extracted with DCM and the combined organic phases were dried over MgSO4 and concentrated to give 977 mg (62%) of 4-formylphenyl 4-(heptyloxy)benzoate INT-12 which was used in the next step without purification. LCMS-ESI (m/z) calculated for C21H24O4: 340; found 341 [M+H]+, tR=11.91 min (Method 2). 1H NMR (400 MHz, DMSO) δ 10.03 (s, 1H), 8.19-7.91 (m, 4H), 7.63-7.41 (m, 2H), 7.24-7.01 (m, 2H), 4.09 (t, J=6.5 Hz, 2H), 1.86-1.62 (m, 2H), 1.50-1.07 (m, 8H), 0.87 (t, J=6.9 Hz, 3H).

1. customPrepared
2. customSolvent was evaporated under high vacuum
3. additionDCM (10 mL) was added
4. customthe reaction mixture evaporated again to dryness
5. dissolutionThe residue was dissolved in DCM (10 mL)
6. stirringto stir at room temperature for 2 h
7. customThe reaction mixture was quenched with NaHCO3 (10 mL)
8. extractionThe aqueous phase was extracted with DCM
9. dry with materialthe combined organic phases were dried over MgSO4
10. concentrationconcentrated

ORD 기록

ord-459a2e39ca9d4a8cb4422878d9165d52

출처 데이터셋

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09278910B2