Hydrochloric Acid → 4-(5-Phenylpentyloxy)-3-methoxy-benzaldehyde

HRID 378975ノート

反応式

HRID 378975 の反応式
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].[C:18]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]OS(C)(=O)=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>CN(C)C=O>[C:18]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:9][C:8]2[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=2[O:6][CH3:7])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 10340Sodium CarbonateHCID 116301071-Methylsulfonyloxy-5-phenylpentane

生成物 1

HCID 216972874-(5-Phenylpentyloxy)-3-methoxy-benzaldehyde収率 97%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of vanillin (12.49 g, 82.1 mmoles) in dimethylformamide was added with Na2CO3 (17.4 g, 164 mmoles) and KI (catalytic amount). The mixture was brought to 90° C. then slowly added with methansulfonic acid 5-phenyl-pentyl ester (24.87 g, 103 mmoles) obtained as described in example 11, in dimethylformamide (40 ml). After 1.5 hours the mixture was poured into 1N HCl and thrice extracted with pentane, anhydrified and dried. The residue was purified by silica gel flash chromatography (eluent: petrolatum/ethyl acetate 9:1), so 7.46 g of the title product were obtained (yield: 97%).

後処理

  1. customwas brought to 90° C.
  2. customobtained
  3. extractionextracted with pentane
  4. customdried
  5. customThe residue was purified by silica gel flash chromatography (eluent: petrolatum/ethyl acetate 9:1)

出典と根拠

ORDレコード
ord-d62ea3f5e5cb47a1a1f930c52d2b8cac
出典データセット
uspto-grants-2001_10
特許番号
US06297257B1

反応ノート

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