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

HRID 1721983Notes

Reaction equation

HRID 1721983 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 (2X) 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) δ 2.6 (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). ##STR150##

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 (2X)
  7. customthe combined extracts dried
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e4f6c515ac5b412b888c1462f6bf90ca
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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