4-(Diethoxymethyl)benzaldehyde → Benzenemethanol, 4-(diethoxymethyl)-

HRID 1509356

反応式

HRID 1509356 の反応式
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C>[CH2:14]([O:13][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)[CH3:15]

参加物

5

反応物 2

HCID 5959934-(Diethoxymethyl)benzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 11063705Benzenemethanol, 4-(diethoxymethyl)-収率 100%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

4-(Diethoxymethyl)benzaldehyde (10 g, 48 mmol) was dissolved in methanol (200 ml) and cooled to 0° C. NaBH4 (4.54 g, 120 mmol, 2.5 eq) was then added slowly and the reaction mixture was stirred for 1 hour, after which the solvent was evaporated. The residue obtained was dissolved in ethyl acetate (100 ml) and water (100 ml), the phases were separated and the organic phase was washed with water (100 ml), dried over magnesium sulphate, and evaporated to yield 1 as a clear oil (10.09 g, 48 mmol, 100%). 1H NMR (300 MHz, CDCl3) δ=7.48 (d, 3J(H,H)=8.1 Hz, 2H, ArCH α to CH2OH), 7.37 (d, 3J(H,H)=8.1 Hz, 2H, ArCH α to CH(OEt)2), 5.51 (s, 1H, CH(OEt)2), 4.70 (d, 3J(H,H)=5.9 Hz, 2H, CH2OH), 3.61 (dq, 3J(H,H)=7.1 Hz, 2J(H,H)=9.5 Hz, 2H, CH2CH3), 3.56 (dq, 3J(H,H)=7.1 Hz, 2J(H,H)=9.5 Hz, 2H, CH2CH3), 1.75 (t, 3J(H,H)=5.9 Hz, 1H, CH2OH), 1.24 (t, 3J(H,H)=7.1 Hz, 6H, CH2CH3); 13C NMR (75 MHz, CDCl3) δ=140.9 (ArCCH2OH), 138.6 (ArCCH(OEt)2), 126.9 (ArCH α to ArCCH2OH), 126.8 (ArCH α to ArCCH(OEt)2), 101.3 (CH(OEt)2), 65.1 (CH2OH), 61.0 (OCH2CH3), 15.2 (OCH2CH3).

後処理

  1. customafter which the solvent was evaporated
  2. customThe residue obtained
  3. customwater (100 ml), the phases were separated
  4. washthe organic phase was washed with water (100 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

出典と根拠

ORDレコード
ord-04fa5ba0ecb847eb909e30a2c4f1f988
出典データセット
uspto-grants-2015_12
特許番号
US09222941B2

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