Tyrosol → HCID 4324878, compound

To a solution of 4-(2-hydroxyethyl)phenol 9.50 g in acetic acid 60 ml is dropped bromine 3.54 ml over a period of 10 minutes on a water bath, and the mixture is stirred for 15 minutes. The reaction mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate layer is washed, dried and concentrated in vacuo. The residue is dissolved in methanol 120 ml and thereto is added potassium carbonate 25 g. The mixture is stirred at room temperature for 5 hours. and then diluted with water and with ethyl acetate. The solution is acidified with concentrated sulfuric acid. The organic layer is extracted with ethyl acetate, washed, dried and concentrated in vacuo. The residue is crystallized from chloroform to give 2-bromo-4-(2-hydroxyethyl)phenol as a slightly brown crystalline powder 9.37 g. mp 83-85° C.

1. extractionextracted with ethyl acetate
2. washThe ethyl acetate layer is washed
3. customdried
4. concentrationconcentrated in vacuo
5. dissolutionThe residue is dissolved in methanol 120 ml
6. additionis added potassium carbonate 25 g
7. stirringThe mixture is stirred at room temperature for 5 hours
8. additionand then diluted with water and with ethyl acetate
9. extractionThe organic layer is extracted with ethyl acetate
10. washwashed
11. customdried
12. concentrationconcentrated in vacuo
13. customThe residue is crystallized from chloroform

ORD record

ord-32bc962136574521aa245c0f6c0e09d1

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07273868B2