Bromocyclopentane → 4-Cyclopentyloxy-3-hydroxybenzaldehyde

HRID 39332

반응식

HRID 39332 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH:11]1(Br)[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1(C)C=CC=CC=1>[CH:11]1([O:10][C:9]2[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[OH:1])[CH2:15][CH2:14][CH2:13][CH2:12]1

참가 물질

6

반응물 3

HCID 8728BromocyclopentaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate2회

생성물 1

HCID 167261494-Cyclopentyloxy-3-hydroxybenzaldehyde

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
77.5 °C

실험 절차

A suspension of 3,4-dihydroxy benzaldehyde (50.0 g, 0.3623 mol), cyclopentyl bromide (135 g, 0.9058 mol) and potassium carbonate (50.0 g, 0.3623 mol) in N,N-dimethylformamide (500 mL) was stirred at about 75-80° C. for about 1.0 hr. 4×12.5 g potassium carbonate was then added after every 1.0 hr. The reaction mixture was cooled to ambient temperature and filtered to remove inorganic materials. The residue obtained after concentration of the filtrate was diluted with toluene (250 mL), and extracted with 5-10% aqueous sodium hydroxide solution (6×50 mL). The combined aqueous layer was acidified to pH about 3 to 5 by 5N aqueous hydrochloric acid solution. The solid which separated was filtered, washed with water and dried to give 4-cyclopentyloxy-3-hydroxy benzaldehyde.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. customto remove inorganic materials
  4. customThe residue obtained after concentration of the filtrate
  5. extractionextracted with 5-10% aqueous sodium hydroxide solution (6×50 mL)
  6. customThe solid which separated
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-89aa6abc2ce546009d22bfdcfac4be8d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524905B2

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