Chloral → 3-(Allyloxy)-4-hydroxybenzaldehyde

HRID 597662

反応式

HRID 597662 の反応式
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])[CH:2]=[CH2:3].[O:12]=[CH:13]C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=1[OH:11])[CH:13]=[O:12])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 6407ChloralHCID 10340Sodium CarbonateHCID 70772Phenol, 2-(2-propenyloxy)-

生成物 1

HCID 155743773-(Allyloxy)-4-hydroxybenzaldehyde

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

149 g (1 mol) of o-allyloxyphenol and 180 g (1.22 mols) if chloral are fused by gentle warming, 100 g of finely powdered sodium carbonate are added at 25° C and the mixture is subsequently stirred for 8 hours. The resulting viscous mass is stored for 5 days at room temperature and then introduced into 500 ml of water. The whole is thoroughly stirred, the water is decanted and washing is repeated three more times, with 250 ml of water at a time. The viscous oil which remains is crude 2-allyloxy-4-(1-hydroxy-2-trichloro-ethyl)-phenol. This is introduced into a solution of 250 g of potassium hydroxide in 500 ml of methanol at 30° C over the course of 2-3 hours and the reaction mixture is left to stand for 3 hours. The alkali metal salts which have precipitated are filtered off and the filtrate is evaporated under reduced pressure. The oily residue is converted into a slurry with ice water, acidified with hydrochloric acid and extracted with chloroform. The chloroform extract is washed with water, dried over sodium sulphate and then filtered through a 3 cm thick layer of Merck silica gel (0.063-0.20). After washing with chloroform, evaporation of the filtrate under reduced pressure and crystallisation of the residue from hexane yields 3-allyloxy-4-hydroxy-benzaldehyde of melting point 66°-67° C.

後処理

  1. additionare added at 25° C
  2. waitThe resulting viscous mass is stored for 5 days at room temperature
  3. stirringThe whole is thoroughly stirred
  4. customthe water is decanted
  5. washwashing
  6. additionThis is introduced into a solution of 250 g of potassium hydroxide in 500 ml of methanol at 30° C over the course of 2-3 hours
  7. waitthe reaction mixture is left
  8. waitto stand for 3 hours
  9. customThe alkali metal salts which have precipitated
  10. filtrationare filtered off
  11. customthe filtrate is evaporated under reduced pressure
  12. extractionextracted with chloroform
  13. extractionThe chloroform extract
  14. washis washed with water
  15. dry with materialdried over sodium sulphate
  16. filtrationfiltered through a 3 cm thick layer of Merck silica gel (0.063-0.20)
  17. washAfter washing with chloroform, evaporation of the filtrate under reduced pressure and crystallisation of the residue from hexane

出典と根拠

ORDレコード
ord-5bdcd1976fb547c28d1a9664e7a6170c
出典データセット
uspto-grants-1977_03
特許番号
US04014920

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