2-Ethylphenol → 3-Ethyl-4-hydroxybenzaldehyde

45.5 g of titanium tetrachloride was dropwise added, under stirring with ice, to a solution obtained by dissolving 14.64 g of 2-ethylphenol in 200 ml of dichloromethane. After the completion of the dropwise addition, 22.76 g of α,α-dichloromethyl methyl ether was dropwise added thereto. The ice bath was removed, and the reaction solution was stirred at room temperature for 2 hours. Then, the reaction solution was poured into a 10% hydrochloric acid aqueous solution, and the mixture was stirred for 2 hours. The reaction mixture was extracted with chloroform. The chloroform layer was washed with water, and then extracted with a 10% sodium hydoxide aqueous solution. The alkali extract layer was washed twice with chloroform, and then acidified to a pH of about 2 by gradually adding concentrated hydrochloric acid. Then, the mixture was extracted with ethyl acetate. The extract was washed sequentially with water and a saturated sodium chloride aqueous solution, and dried over sodium sulfate. Then, the solvent was distilled off to obtain a dark reddish purple oily substance. This product was purified by silica gel column chromatography by using benzene-ethyl acetate (16 : 1, v/v) as the developer, whereby 6.90 g of the above identified compound was obtained as a pale red oily substance.

1. customobtained
2. additionwas dropwise added
3. customThe ice bath was removed
4. stirringthe reaction solution was stirred at room temperature for 2 hours
5. additionThen, the reaction solution was poured into a 10% hydrochloric acid aqueous solution
6. stirringthe mixture was stirred for 2 hours
7. extractionThe reaction mixture was extracted with chloroform
8. washThe chloroform layer was washed with water
9. extractionextracted with a 10% sodium hydoxide aqueous solution
10. washThe alkali extract layer was washed twice with chloroform
11. additionby gradually adding concentrated hydrochloric acid
12. extractionThen, the mixture was extracted with ethyl acetate
13. washThe extract was washed sequentially with water
14. dry with materiala saturated sodium chloride aqueous solution, and dried over sodium sulfate
15. distillationThen, the solvent was distilled off
16. customto obtain a dark reddish purple oily substance
17. customThis product was purified by silica gel column chromatography
18. customwas obtained as a pale red oily substance

ORD record

ord-b188f3218bd24867afb122fcb4bfe439

Source dataset

uspto-grants-1988_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04783462