Benzyl Bromide → 2-(Benzyloxy)-3-methoxybenzaldehyde

HRID 260070

反応式

HRID 260070 の反応式
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:8][O:7][C:6]1[C:4]([O:5][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 8991o-VanillinHCID 11430Potassium Carbonate

生成物 1

HCID 12680872-(Benzyloxy)-3-methoxybenzaldehyde収率 93%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 196.0 g (1.30 mole) of o-vanillin (Aldrich), 200 g of benzyl bromide (Aldrich), 500 g of anhydrous potassium carbonate and 1,500 mL of absolute ethanol is heated, with stirring, at reflux for 6 hours. After cooling, the supernatant is decanted and the remainder is filtered. The combined filtrate and supernatant is concentrated at reduced pressure to remove solvent. The remaining oil is extracted into 1 L of ether. The ether solution is washed with 500 mL of water, 600 mL of 1% potassium hydroxide solution, and 500 mL of water and then dried (potassium carbonate) and concentrated to give 263.4 g (84% yield) of product; mp 41°-43° C. Reported mp, 43° C. (Chem. Abstr. 62:16110a).

後処理

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. temperatureAfter cooling
  4. customthe supernatant is decanted
  5. filtrationthe remainder is filtered
  6. concentrationThe combined filtrate and supernatant is concentrated at reduced pressure
  7. customto remove solvent
  8. extractionThe remaining oil is extracted into 1 L of ether
  9. washThe ether solution is washed with 500 mL of water, 600 mL of 1% potassium hydroxide solution, and 500 mL of water
  10. dry with materialdried (potassium carbonate)
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-1c7d521c149d4a3c968ce07c145bcd86
出典データセット
uspto-grants-1996_06
特許番号
US05525614

関連ノート

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