1-Naphthaldehyde → HCID 54418911, compound

HRID 2188204Notes

Reaction equation

HRID 2188204 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CC(C)([O-:16])C.[K+].[O:19]1[CH2:23][CH2:22][CH2:21]C1>>[C:1]1([CH2:11][CH:21]=[CH:22][C:23]([OH:19])=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 61951-NaphthaldehydeHCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 54418911HCID 54418911, compound

Procedure

To a mixture of 3-triphenylphosphorylpropionic acid chloride (12.40 g) and 1-naphthaldehyde in dry tetrahydrofuran (30 cm3) at 0° C. under an atmosphere of nitrogen was added a solution of potassium tert-butoxide (7.54 g) in tetrahydrofuran (30 cm3) over a period of 1 h. The reaction was allowed to warm to room temperature and stirred for a further 12 h before it was quenched with water (40 cm3) and extracted with diethyl ether (2×40 cm3). The aqueous portion was acidified with hydrochloric acid (5 M) and extracted into dichloromethane (3×40 cm3). The organic extracts were dried (Na2SO4) and the solvent was removed under reduced pressure to give a brown oil that crystallised on standing. The product was re-crystallised from aqueous ethyl alcohol to afford the title compound (3.96 g).

Workup

  1. customwas quenched with water (40 cm3)
  2. extractionextracted with diethyl ether (2×40 cm3)
  3. extractionextracted into dichloromethane (3×40 cm3)
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. customthe solvent was removed under reduced pressure
  6. customto give a brown oil that
  7. customcrystallised
  8. customThe product was re-crystallised from aqueous ethyl alcohol

Sources & evidence

ORD record
ord-2c97b767488b4b7b8b4a21bb2e75d354
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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