Benzaldehyde → HCID 18960336, compound

HRID 1707923Notes

Reaction equation

HRID 1707923 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[C:16]([O:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:25](=[O:32])C1C=CC=CC=1.[C:33]1(C)C=CC=CC=1>CO.C(OC)(OC)OC>[CH3:33][O:12][CH:11]([O:32][CH3:25])[C:10]1[CH:13]=[CH:14][CH:15]=[C:16]([O:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9]=1[O:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 1140TolueneHCID 18960345HCID 18960345, compound

Product 1

HCID 18960336HCID 18960336, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 9005Trimethyl orthoformateSolvent

Procedure

Three g (9 mmol) of 2,3-bis-tert.-butoxycarbonyloxy-benzaldehyde were dissolved at room temperature in 10 ml of methanol and 1.2 ml of trimethyl orthoformate. For complete dissolution of the benzaldehyde derivative, 1.5 ml of toluene were added. This was followed by the addition of 3.75 mg of RhCl3 [CH3C(CH2PPh2)3 ] as catalyst. The mixture was then stirred overnight at room temperature. The solvents were separated off by steam distillation and the oily residue was taken up in a little toluene. The undissolved rhodium catalyst was filtered off over a G-4 frit. After the toluene had been stripped off under reduced pressure, the product was dried in an oil pump vacuum.

Workup

  1. additionwere added
  2. customThe solvents were separated off by steam distillation
  3. filtrationThe undissolved rhodium catalyst was filtered off over a G-4 frit
  4. customthe product was dried in an oil pump vacuum

Sources & evidence

ORD record
ord-530afe2a2df14a12a854afdb63032089
Source dataset
uspto-grants-1994_10
Patent number
US05356752

Reaction notes

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