4-Hydroxybenzaldehyde → HCID 58234675, compound

HRID 68241Notes

Reaction equation

HRID 68241 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[N:16]1([C:22](Cl)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:16]1([C:22]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 1049PyridineHCID 848104-Morpholinecarbonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 58234675HCID 58234675, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 250 mL dry round bottom flask were added 4-hydroxybenzaldehyde (6.11 g, 50.0 mmol), anhydrous CH2Cl2 (80 mL) and pyridine (4.86 mL, 60.0 mmol). The mixture was stirred in an ice-water, then 4-morpholinecarbonyl chloride (6.12 mL, 52.5 mmol) was added. The mixture was stirred and warmed slowly to room temperature, then stirred at room temperature overnight. An aqueous solution of 5% NaHCO3 (100 mL) was added to the reaction mixture. The CH2Cl2 layer was separated, and the aqueous layer was extracted continually with CH2Cl2 (50 mL×2). The combined CH2Cl2 solution was dried over Na2SO4. Removal of the solvent gave 4-formylphenyl morpholine-4-carboxylate (8.80 g) as white solid. Yield: 75%. 1H NMR (CDCl3, 300 MHz): δ=9.97 (s, 1H), 7.90 (d, J=9.0 Hz, 2H), 7.30 (d, J=9.0 Hz, 2H), 3.77-3.57 (m, 6H). 13C NMR (CDCl3, 75.5 MHz, mixture of two isomers): δ=191.0, 156.0, 152.6, 133.6, 131.1, 122.3, 66.5, 66.4, 45.0, 44.2.

Workup

  1. customTo a 250 mL dry round bottom flask
  2. stirringstirred at room temperature overnight
  3. customThe CH2Cl2 layer was separated
  4. extractionthe aqueous layer was extracted continually with CH2Cl2 (50 mL×2)
  5. dry with materialThe combined CH2Cl2 solution was dried over Na2SO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-f5121c7f80da4e939e5ce52f3a9fc207
Source dataset
uspto-grants-2014_09
Patent number
US08822435B2

Reaction notes

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