2-Propenoic acid, 3-(4-formylphenyl)- → HCID 54422591, compound

A solution of NaBH4 (0.53 g, 14 mmol) in THF/H2O (4:1) (12 mL) was added dropwise to an ice-cold stirred solution of 4-formylcinnamic acid (2.47 g, 14 mmol) in THF (25 mL), and the mixture was stirred at room temperature for 3 h. The reaction was quenched by adding 4 N HCl (20 mL), and the THF was removed by a rotary evaporator. The solid residue was treated with H2O (20 mL), and extracted with EtOAc (4×50 mL). The EtOAc extracts were washed with H2O (50 mL) and brine (50 mL), and dried. The crude product was recrystallized from EtOAc to afford pure 4-hydroxymethylcinnamic acid 124 (1.3 g, 52% yield) as yellow solid, with its identity verified by 1H NMR (300 MHz, CD3OD).

1. customThe reaction was quenched
2. additionby adding 4 N HCl (20 mL)
3. customthe THF was removed by a rotary evaporator
4. additionThe solid residue was treated with H2O (20 mL)
5. extractionextracted with EtOAc (4×50 mL)
6. washThe EtOAc extracts were washed with H2O (50 mL) and brine (50 mL)
7. customdried
8. customThe crude product was recrystallized from EtOAc

ORD record

ord-cd9d41798132444b952ba84fc71795a2

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260382B2