Hydrochloric Acid → 5-[4-(Benzyloxy)-3-methoxyphenyl]penta-2,4-dienoic acid

HRID 1974697Notes

Reaction equation

HRID 1974697 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:24]CC)(=[O:23])/[CH:20]=[CH:21]/[CH3:22].CC(C)([O-])C.[K+].[OH-].[Na+].Cl>CN1CCCC1=O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:22][CH:21]=[CH:20][C:19]([OH:24])=[O:23])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 429065Ethyl trans-crotonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 542250435-[4-(Benzyloxy)-3-methoxyphenyl]penta-2,4-dienoic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution containing 260 g of 4-benzyloxy-3-methoxybenzaldehyde and 200 ml of ethyl crotonate in 1200 ml of N-methylpyrrolidone was gradually added while stirring and cooling at 0° C. 149.6 g of potassium tert.-butoxide. The solution was stirred for 0.5 h after which 200 ml of 10N NaOH-solution was added and stirred for 0.5 h more at 0° C. The reaction mixture was added to a mixture of hydrochloric acid and ice. The semisolid product was separated and used without purification to the next step.

Workup

  1. additionwas gradually added
  2. additionwas added
  3. stirringstirred for 0.5 h more at 0° C
  4. customThe semisolid product was separated
  5. customused without purification to the next step

Sources & evidence

ORD record
ord-842d31f28bcd425a99252284acebfe40
Source dataset
uspto-grants-1994_02
Patent number
US05283352

Reaction notes

Loading…