Potassium Carbonate → 5-[[6-([1,1'-Biphenyl]-4-yloxy) hexyl]oxy]-2-hydroxybenzoic acid methyl ester

HRID 488322노트

반응식

HRID 488322 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:11].[C:13]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([O:10][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:16]2[CH:15]=[CH:14][C:13]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:18][CH:17]=2)[CH:7]=[CH:6][C:5]=1[OH:11]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 75077Methyl GentisateHCID 234323996-([1,1'-Biphenyl]-4-yloxy)hexyl bromide

생성물 1

HCID 545134655-[[6-([1,1'-Biphenyl]-4-yloxy) hexyl]oxy]-2-hydroxybenzoic acid methyl ester수율 56%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1.0 g (6 mmol) of 2,5-dihydroxybenzoic acid methyl ester, 2.0 g (6 mmol) of 6-([1,1'-biphenyl]-4-yloxy)hexyl bromide and 1.24 g (9 mmol) of potassium carbonate in 50 ml of acetone and 5 ml of DMF was stirred at reflux for 27 hours. The solvents were removed at reduced pressure, water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was purified by chromatography on 40 g of silica gel using 50% toluene-hexane to give 1.4 g (56% yield, mp 91°-92°) of 5-[[6-([1,1'-biphenyl]4-yloxy)hexyl]oxy]-2-hydroxybenzoic acid methyl ester. The structure was confirmed by nmr and mass spectra.

후처리

  1. temperatureat reflux for 27 hours
  2. customThe solvents were removed at reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas purified by chromatography on 40 g of silica gel using 50% toluene-hexane

출처 및 근거

ORD 기록
ord-a19262170b614899affda64e2eb4271a
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05298652

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