Hydrochloric Acid → 2-Hydroxy-4-methylbenzaldehyde

HRID 22928

반응식

HRID 22928 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[Sn](Cl)(Cl)Cl.[CH2:14]=[O:15].Cl>C1(C)C=CC=CC=1.O>[OH:8][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[CH:14]=[O:15]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 342M-CresolHCID 712FormaldehydeHCID 24287Tin tetrachloride

생성물 1

HCID 612002-Hydroxy-4-methylbenzaldehyde수율 25.5%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 3-methyl-phenol (1 g, 9.2 mmol) in toluene (5 ml) at room temperature under nitrogen was added SnCl4 (241 mg, 0.92 mmol) and tri-nbutylamine (0.6 ml, 2.77 mmol). After 20 min, paraformaldehyde (611 mg, 20.3 mmol) was added and the whole stirred at 100° C. for 16 h. The reaction mixture was diluted with water (20 ml) and acidified with 2N HCl to pH2. The solution was extracted with ether (25 ml), washed with brine (20 ml), dried (MgSO4) filtered and evaporated to a brown oil. This oil was purified by column chromatography using 5% EtOAc in pentane as eluant to provide the title product (319 mg, 25%); 1HNMR (400 MHz, CDCl3) δ: 2.3 (s, 3H), 6.75 (m, 2H), 7.35 (d, 1H), 9.75 (s, 1H), 11.00 (s, 1H).

후처리

  1. extractionThe solution was extracted with ether (25 ml)
  2. washwashed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to a brown oil
  6. customThis oil was purified by column chromatography

출처 및 근거

ORD 기록
ord-967ddfe73b30491d9915c6116112b85f
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849649B2

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