Trimethyl orthoformate → Benzene, 1-(dimethoxymethyl)-3-methoxy-

HRID 483677Notes

Reaction equation

HRID 483677 reaction equation
C(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[CH:11]([O:16][CH3:17])([O:14][CH3:15])OC.C(=O)(O)[O-].[Na+]>CO>[CH3:17][O:16][CH:11]([O:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 115693-MethoxybenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 10910282Benzene, 1-(dimethoxymethyl)-3-methoxy-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

m-Anisaldehyde (204.3 g, 1.5 mol) was placed in a 1 liter flask under an argon atmosphere. Trimethyl orthoformate (191 g, 1.8 mol) was added quickly, followed by 150 ml anhydrous methanol. Amberlyst XN-1010 resin (2.1 g, Aldrich Chemical Co.), which had been previously boiled with methanol was added. The mixture was stirred at room temperature for 22 hours with the exclusion of moisture. Sodium bicarbonate (1.5 g) was added with stirring. After 20 minutes the mixture was filtered under vacuum into a 2 liter flask which was placed on the rotory evaporator with the water bath temperature at 40° C. Over 30 minutes the bath was heated to 80° to produce a clear, colorless oil. With magnetic stirring, the oil was pumped at 65° under vacuum (2 mm Hg) for 30 minutes. The resulting product weighted 272.5 g (99.8%). I.R. (near, cm-1): 2935, 2824, 1598, 1584, 1350, 1258, 1100, 1050, 984, 772. 1HNMR (400 MHz, CDCl3) δ 3.33 (6H, s, OCH3); 3.81 (3H, s, ArOCH3); 5.35 (1H, s, ArCH(OCH3)2 ; 6.87 (1H, br d, 8.1 Hz); 7.00-7.03 (2H, m); 7.27 (1H, t, 8.1 Hz). These data indicated that the product was pure enough for use in the next step and were consistent with the following structure: ##STR27##

Workup

  1. additionwas added
  2. stirringwith stirring
  3. filtrationAfter 20 minutes the mixture was filtered under vacuum into a 2 liter flask which
  4. customwas placed on the rotory evaporator with the water bath temperature at 40° C
  5. temperatureOver 30 minutes the bath was heated to 80°
  6. customto produce a clear, colorless oil
  7. waitWith magnetic stirring, the oil was pumped at 65° under vacuum (2 mm Hg) for 30 minutes

Sources & evidence

ORD record
ord-7ed32db73b724b0ba7b6e08c6d3ac740
Source dataset
uspto-grants-1993_07
Patent number
US05225584

Reaction notes

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