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

HRID 1509356

반응식

HRID 1509356 반응식
[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]

참가 물질

5

반응물 2

HCID 5959934-(Diethoxymethyl)benzaldehydeHCID 4311764Sodium borohydride

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-04fa5ba0ecb847eb909e30a2c4f1f988
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09222941B2

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