Hydrochloric Acid → 2-Docosyloxy-4-methoxybenzyl alcohol

HRID 537598

反応式

HRID 537598 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(=O)([O-])[O-].[K+].[K+].Cl>C(Cl)(Cl)Cl.CN(C=O)C>[CH2:34]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 813551-Bromodocosane

生成物 1

HCID 532572102-Docosyloxy-4-methoxybenzyl alcohol収率 64.4%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

2-Hydroxy-4-methoxybenzaldehyde (5 g, 32.9 mmol), 1-bromodocosane (16.6 g, 42.7 mmol) and potassium carbonate (14.8 g, 107 mmol) were mixed with DMF (150 ml), and the mixture was stirred at 100° C. for 7 hr. Chloroform (400 ml) and 1N hydrochloric acid (300 ml) were added to the reaction mixture, and the mixture was washed. The organic layer was washed successively with 1N hydrochloric acid and saturated brine. The organic layer was concentrated and slurry-washed with methanol. The precipitate was collected by filtration and dried under reduced pressure. The obtained dried crystals were dissolved in THF (150 ml), sodium borohydride (3.7 g) was added, and the mixture was stirred at 40° C. for 3 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was concentrated. The mixture was extracted with chloroform, and washed successively with aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was concentrated. The obtained residue was washed with acetonitrile, and the precipitate was collected by filtration and dried under reduced pressure to give 2-docosyloxy-4-methoxybenzyl alcohol (9.8 g).

後処理

  1. washthe mixture was washed
  2. washThe organic layer was washed successively with 1N hydrochloric acid and saturated brine
  3. concentrationThe organic layer was concentrated
  4. washslurry-washed with methanol
  5. filtrationThe precipitate was collected by filtration
  6. customdried under reduced pressure
  7. customThe obtained dried crystals
  8. dissolutionwere dissolved in THF (150 ml)
  9. additionsodium borohydride (3.7 g) was added
  10. stirringthe mixture was stirred at 40° C. for 3 hr
  11. addition1N Hydrochloric acid was added to the reaction mixture
  12. concentrationthe mixture was concentrated
  13. extractionThe mixture was extracted with chloroform
  14. washwashed successively with aqueous sodium hydrogen carbonate solution and saturated brine
  15. concentrationThe organic layer was concentrated
  16. washThe obtained residue was washed with acetonitrile
  17. filtrationthe precipitate was collected by filtration
  18. customdried under reduced pressure

出典と根拠

ORDレコード
ord-1e8858f487b24899b0dcdb987cbceddc
出典データセット
uspto-grants-2014_10
特許番号
US08859732B2

関連ノート

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