Benzaldehyde → {3-[2-(3,4-Dimethoxyphenyl)ethyl]-2-phenyl-1,3-oxazolidin-5-yl}methanol

HRID 235935Notes

Reaction equation

HRID 235935 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:19](O)(=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)C1C=CC=CC=1>C1C=CC=CC=1>[C:20]1([CH:19]2[N:13]([CH2:12][CH2:11][C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:14][CH:15]([CH2:16][OH:17])[O:18]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 12875895HCID 12875895, compound

Product 1

HCID 12877852{3-[2-(3,4-Dimethoxyphenyl)ethyl]-2-phenyl-1,3-oxazolidin-5-yl}methanolYield 2,750%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3 (195 g, 0.76 mol), benzoic acid (3.0 g), benzaldehyde (270 ml), C6H6 (180 ml) was heated to reflux while collecting the H2O in a Dean-Stark trap. After 21/2 hours, 13 ml of H2O was collected and the solution cooled, washed with saturated Na2CO3. The aqueous layer was washed with CHCl3 (2×) and the combined extracts dried, filtered and concentrated to dryness to yield 232 g of 5 which contains 26 mol% benzaldehyde. This corresponds to 209 g of 5; 'H NMR (CDCl3) δ2.6 (6H, m), 3.4 (2H, m), 3.75 (7H, d, m), 4.3 (1H, m), 4.8 (1H, d), 6.7 (3H, m), 7.4 (5H, bs). ##STR142##

Workup

  1. temperatureto reflux
  2. customwhile collecting the H2O in a Dean-Stark trap
  3. customAfter 21/2 hours, 13 ml of H2O was collected
  4. temperaturethe solution cooled
  5. washwashed with saturated Na2CO3
  6. washThe aqueous layer was washed with CHCl3 (2×)
  7. customthe combined extracts dried
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5f4179319cd2490dac804a4074d84c30
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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