4-Hydroxybenzaldehyde → p-((Trimethylsilyl)oxy)benzaldehyde

HRID 128784

반응식

HRID 128784 반응식
C(N(CC)CC)C.[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.Cl[Si:18]([CH3:21])([CH3:20])[CH3:19]>CCOCC>[CH3:19][Si:18]([CH3:21])([CH3:20])[O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 6397ChlorotrimethylsilaneHCID 8471Triethylamine

생성물 1

HCID 70536p-((Trimethylsilyl)oxy)benzaldehyde

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Triethylamine (42 ml) is added dropwise to a stirred solution of 4-hydroxybenzaldehyde (33.5 g) and chlorotrimethylsilane (42 ml) in ether (300 ml). After 15 min, the mixture is filtered through diatomaceous earth and the filtrate is concentrated and distilled in vacuo, providing 4-(trimethylsiloxy)benzaldehyde as a colorless oil (43 g). This material is reacted with methoxymethyl triphenylphosphonium chloride and potassium tert-butoxide in THF, using the procedure described in Example 1 (A) above, to provide 1-(2-methoxyethenyl)-4-(trimethylsiloxy)benzene (35%) as a colorless oil after distillation in vacuo, as a mixture of (E) and (Z) isomers. This material (3.0 g) is dissolved in methanol (30 ml) containing methanesulfonic acid (0.4 ml), and the solution is refluxed for 3 hr. Sodium bicarbonate (8 ml of 1.0N solution) is added, and the mixture is concentrated in vacuo. The residue is taken up in ethyl acetate, dried, and concentrated to provide 4-[(2,2-dimethoxy)ethyl]phenol as a pale red oil (2.4 g).

후처리

  1. filtrationthe mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate is concentrated
  3. distillationdistilled in vacuo

출처 및 근거

ORD 기록
ord-37274ef06ac5448cba0b03217495d634
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464865

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