Citric Acid → 1-Naphthaldehyde

HRID 1675729Notes

Reaction equation

HRID 1675729 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:21][OH:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.CCN(CC)CC.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.O>[C:11]1([CH:21]=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 311Citric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 209081-NaphthalenemethanolHCID 65578Oxalyl chloride

Product 1

HCID 61951-NaphthaldehydeYield 98.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cold (−78° C.) solution of oxalyl chloride (6.9 mL, 0.079 mol) in dry CH2Cl2 (200 mL) was added dropwise dry DMSO (11.2 mL, 0.158 mol). The mixture was stirred for 10 min, and then a solution of 1-naphthalenemethanol (10.0 g, 0.063 mol) in dry CH2Cl2 (40 mL) was added over 15 min. The mixture was stirred for 10 min, and then Et3N (44 mL, 0.316 mol) was added slowly. The reaction mixture was allowed to warm to room temperature. After 3.5 h, to the pale yellow heterogeneous mixture was added 10% aqueous citric acid (30 mL) and water (100 mL). The organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL), dried (anhydrous MgSO4), filtered, and concentrated. Ether-hexane (1:1) was added, and the mixture was filtered. Concentration provided a pale orange oil (9.7 g).

Workup

  1. stirringThe mixture was stirred for 10 min
  2. waitAfter 3.5 h
  3. washThe organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL)
  4. dry with materialdried (anhydrous MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionEther-hexane (1:1) was added
  8. filtrationthe mixture was filtered
  9. concentrationConcentration

Sources & evidence

ORD record
ord-af36b53d1dab4ba8b97000e30b738890
Source dataset
uspto-grants-2011_08
Patent number
US08003791B2

Reaction notes

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