Benzyl Bromide → 4-(Benzyloxy)-1,2-benzenediol

HRID 1614723

반응식

HRID 1614723 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[OH:9].[H-].[Na+].B(OCC)(OCC)OCC.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([O:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([OH:9])[CH:4]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 9009Triethyl borateHCID 107871,2,4-BenzenetriolHCID 24758Sodium hydride

생성물 1

HCID 155069714-(Benzyloxy)-1,2-benzenediol수율 58%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

1.37 g of 1,2,4-trihydroxy benzene and 30 ml of anhydrous dimethylformamide were mixed together under an inert gas atmosphere and then 0.984 g of sodium hydride in suspension at 53% in oil was added at 15°-20° C. The mixture was stirred for one hour and 1.906 ml of triethyl borate were added. The mixture was stirred for one hour, and 1.29 ml of benzyl bromide in solution in 20 ml of dimethylformamide were added over 2 hours. The mixture was stirred for 16 hours at ambient temperature and then was poured into a water-ice-N hydrochloric acid mixture. Extraction took place with ethyl acetate followed by evaporation to dryness. The residue was washed with petroleum ether, and chromatographed on silica eluting with a cyclohexane-ethyl acetate (6-4) mixture to obtain 1.36 g of the crystallized expected product (Yield: 58%).

후처리

  1. stirringThe mixture was stirred for one hour
  2. stirringThe mixture was stirred for 16 hours at ambient temperature
  3. extractionExtraction
  4. customfollowed by evaporation to dryness
  5. washThe residue was washed with petroleum ether
  6. customchromatographed on silica eluting with a cyclohexane-ethyl acetate (6-4) mixture
  7. customto obtain 1.36 g of the

출처 및 근거

ORD 기록
ord-9fd5685655574b3aaa8630db1cb685b6
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05198571

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