Bromocyclopentane → 4-Cyclopentyloxy-3-hydroxybenzaldehyde

HRID 39332

反応式

HRID 39332 の反応式
[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

参加物

6

反応物 3

HCID 8728BromocyclopentaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate2 回

生成物 1

HCID 167261494-Cyclopentyloxy-3-hydroxybenzaldehyde

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
77.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-89aa6abc2ce546009d22bfdcfac4be8d
出典データセット
uspto-grants-2013_09
特許番号
US08524905B2

関連ノート

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