4-Hydroxybenzaldehyde → 4-(6-Hydroxyhexoxy)benzaldehyde

HRID 970250ノート

反応式

HRID 970250 の反応式
[OH-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[I-].[Na+].Cl[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]>O.C(O)C>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 748286-Chloro-1-hexanol

生成物 1

HCID 150510824-(6-Hydroxyhexoxy)benzaldehyde収率 91%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of 40 g (1 mole) of sodium hydroxide in 60 ml of water and 400 ml of ethanol were added 122.12 g (1 mole) of 4-hydroxybenzaldehyde, 30 g of sodium iodide and 136.62 g (1 mole) of 1-chloro-6-hydroxyhexane. The mixture was heated at reflux for 24 hours under a nitrogen atmosphere. After cooling, the mixture was filtered and the solvent was removed under reduced pressure. Water (400 ml) was added to the residue and the mixture was extracted twice with 400 ml of ethyl acetate. The ethyl acetate layers were extracted twice with 200 ml of 5% aq. sodium hydroxide, and once with 200 ml of brine, dried over magnesium sulfate, and the solvent was evaporated. A brown oil (202 g, 91%) was obtained, which crystallized slowly.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours under a nitrogen atmosphere
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe solvent was removed under reduced pressure
  6. additionWater (400 ml) was added to the residue
  7. extractionthe mixture was extracted twice with 400 ml of ethyl acetate
  8. extractionThe ethyl acetate layers were extracted twice with 200 ml of 5% aq. sodium hydroxide
  9. dry with materialonce with 200 ml of brine, dried over magnesium sulfate
  10. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-c9c9bdf946be4a7fb3eab5016f1e6009
出典データセット
uspto-grants-2007_12
特許番号
US07311948B2

反応ノート

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