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

HRID 1509357

반응식

HRID 1509357 반응식
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)C>C1COCC1.Cl.C(OCC)(=O)C.O>[OH:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH:4]=[O:3])=[CH:6][CH:7]=1

참가 물질

6

반응물 1

HCID 11063705Benzenemethanol, 4-(diethoxymethyl)-

생성물 1

HCID 5563304-(Hydroxymethyl)benzaldehyde수율 100%

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Alcohol 1 (10.09 g, 48 mmol) was dissolved in a mixture of THF (100 ml) and 2 M HCl (100 ml) and stirred for 1 hour. The solvent was evaporated and 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 2 as a white solid (6.54 g, 48 mmol, 100%). Rf=0.54 (ethyl acetate/chloroform, 1:1); νmax=3327, 1689, 1607, 1206, 1010, 823 cm−1; 1H NMR (250 MHz, CDCl3) δ=10.02 (s, 1H, CHO), 7.89 (d, 3J(H,H)=8.1 Hz, 2H, ArCH α to CHO), 7.54 (d, 3J(H,H)=8.1 Hz, 2H, ArCH α to CH2OH), 4.82 (d, 3J(H,H)=5.9 Hz, 2H, CH2OH), 1.94 (t, 3J(H,H)=5.9 Hz, 1H, CH2OH); 13C NMR (75 MHz, CDCl3) δ=192.0 (CHO), 147.7 (ArCCOH), 135.7 (ArCCHO), 130.0 (ArCH α to ArCCHO), 127.0 (ArCH α to ArCCH2OH), 64.6 (CH2OH); HRMS (ESI−): m/z calculated for C8H7O2 [M−H]−: 135.0446, found 135.0448; elemental analysis calcd (%) for C8H8O2 (136.15): C, 70.57; H, 5.92. found: C, 70.70; H, 6.00.

후처리

  1. customThe solvent was evaporated
  2. customthe residue obtained
  3. customThe 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-cbdc903c41d74e9c9405b91d6dcd16fd
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09222941B2

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