Formaldehyde → 3-Tert-butyl-2-hydroxy-5-methylbenzaldehyde

HRID 1062518

반응식

HRID 1062518 반응식
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].C([Mg]Br)C.[CH2:17]=[O:18].C(N(CC)CC)C>C1(C)C=CC=CC=1.CCOCC.C1COCC1>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH:17]=[O:18])[C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 170042-tert-Butyl-4-methylphenolHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 47711753-Tert-butyl-2-hydroxy-5-methylbenzaldehyde수율 65%

시약·촉매·용매 3

HCID 1140Toluene용매2회HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

Into a 1 liter reactor thoroughly dried and purged with nitrogen, 9.68 g (58.93 mmol) of 2-tert-butyl-4-methylphenol and 100 ml of THF were introduced. To the reactor, 23.00 ml of an ether solution containing 69.00 mmol of ethylmagnesium bromide was dropwise added at 0° C. over a period of 30 minutes, then the temperature of the system was slowly raised to room temperature, and the reaction solution was stirred at room temperature for 1 hour. Then, 100 ml of toluene was added, and the system was heated to 95° C. to distill off a mixed solution of ether and THF, whereby an opaque white slurry was obtained. After the slurry was cooled to room temperature, 100 ml of toluene, 4.50 g (149.90 mmol) of paraformaldehyde and 12.50 ml (89.93 mmol) of triethylamine were added, followed by stirring at 95° C. for 2 hours. The reaction solution was allowed to cool to room temperature and then quenched with 300 ml of 1N hydrochloric acid. The organic layer was concentrated and purified by a silica gel column to obtain 7.36 g (yield: 65%) of 3-t-butyl-5-methylsalicylaldehyde.

후처리

  1. customInto a 1 liter reactor thoroughly dried
  2. additionwere introduced
  3. additionwas dropwise added at 0° C. over a period of 30 minutes
  4. temperaturethe system was heated to 95° C.
  5. distillationto distill off a mixed solution of ether and THF, whereby an opaque white slurry
  6. customwas obtained
  7. temperatureAfter the slurry was cooled to room temperature
  8. stirringby stirring at 95° C. for 2 hours
  9. temperatureto cool to room temperature
  10. customquenched with 300 ml of 1N hydrochloric acid
  11. concentrationThe organic layer was concentrated
  12. custompurified by a silica gel column

출처 및 근거

ORD 기록
ord-98191c4901724898b25f714cd6e118b6
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962890B2

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