Methanol → Methyl 4-(benzyloxy)benzoate

HRID 467237

반응식

HRID 467237 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CO>C1COCC1>[CH2:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 7456MethylparabenHCID 7498Benzyl BromideHCID 24758Sodium hydride

생성물 1

HCID 299810Methyl 4-(benzyloxy)benzoate수율 24%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 75 g of methyl 4-hydroxybenzoate in 700 ml THF at 22° C. were added 19.7 g of a 60% dispersion of sodium hydride in mineral oil. After the mixture was stirred for 90 minutes, 84.3 g of benzyl bromide was added dropwise. The reaction was heated at reflux for 18 hours, cooled to room temperature and 50 ml methanol was added. The mixture was evaporated and the resulting residue extracted with three portions of ethyl acetate. The combined organic extracts were washed with water and brine, dried over magnesium sulfate and evaporated to a solid. Recrystallization from cold methanol gave 28.7 g of the title compound: 300 MHz 1H NMR (CDCl3) δ3.96 (s, 3 H), 5.19 (s, 2 H), 7.05 (d, J=9 Hz, 2 H), 7.42 (s, 5 H), 8.05 (d, J=9 Hz, 2 H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 hours
  3. customThe mixture was evaporated
  4. extractionthe resulting residue extracted with three portions of ethyl acetate
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to a solid
  8. customRecrystallization from cold methanol

출처 및 근거

ORD 기록
ord-cb4462c653234d71aa287758a817daa4
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05159079

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