4-Hydroxybenzyl Alcohol → p-Hydroxymethylphenyl 4-vinylbenzyl ether

HRID 248610

반응식

HRID 248610 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[OH-].[K+].C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[CH:28]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1)=[CH2:29]>C(O)C>[CH:28]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=2)=[CH:32][CH:31]=1)=[CH2:29]

참가 물질

6

반응물 4

HCID 1254-Hydroxybenzyl AlcoholHCID 14797Potassium HydroxideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 74126p-Vinylbenzyl chloride

생성물 1

HCID 19105443p-Hydroxymethylphenyl 4-vinylbenzyl ether수율 77%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 4-hydroxybenzyl alcohol (56.7 g, 0.459 molar), 85% potassium hydroxide (32.4 g, 0.459 molar) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (600 ml) was stirred at room temperature for 30 minutes. To this mixture was added 4-vinylbenzylchloride (70.5 g, 0.459 molar) very rapidly and it was then heated to 80° C. for 6 hours and stirred at ambient temperature overnight. The mixture was cooled, filtered and the solvent reduced to 300 ml by placing on a rotary evaporator. The solution was then placed in the freezer overnight. The next day the product was filtered to give a white solid. This material was recrystallized from methanol/dichloromethane (2/1) to give a white solid: m.p. of 110°-111.5° C. Yield of 77%. Analysis calculated for C16H16O2 : C, 79.97, H, 6.71. Found: C, 79.31, H, 6.69. 1H NMR (CDCl3) δ 2.55 (broad s, 1H, OH), 4.5 (s, 2H, CH2OH), 5.08 (s, 2H, ArCH2OAr), 5.25+5.75 (AB quartet, 2H, CH2 =), 6.8 (m, 1H, CH=), 6.8-7.6 (m, 8H, ArH's).

후처리

  1. temperatureit was then heated to 80° C. for 6 hours
  2. stirringstirred at ambient temperature overnight
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customby placing on a rotary evaporator
  6. customwas then placed in the freezer overnight
  7. filtrationThe next day the product was filtered
  8. customto give a white solid
  9. customThis material was recrystallized from methanol/dichloromethane (2/1)
  10. customto give a white solid

출처 및 근거

ORD 기록
ord-745272d7f7224302ac0e5a9f6558b941
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210289

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