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

HRID 128784

Reaction equation

HRID 128784 reaction equation
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

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 6397ChlorotrimethylsilaneHCID 8471Triethylamine

Product 1

HCID 70536p-((Trimethylsilyl)oxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-37274ef06ac5448cba0b03217495d634
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Linked notes

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