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

HRID 1757633Notes

Reaction equation

HRID 1757633 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 200ml of ethyl crotonate in 1200 ml of N-methylpyrrolidone was gradually addedwhile stirring and cooling at 0° C. 149.6 g of potassium tert.-butoxide. The solution was stirred for 0.5 h after which 200ml 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 added
  2. stirringstirred for 0.5 h more at 0° C
  3. customThe semisolid product was separated
  4. customused without purification to the next step

Sources & evidence

ORD record
ord-3c4102f7257d4431b68451e7156f02b2
Source dataset
uspto-grants-1995_08
Patent number
US05446194

Reaction notes

Loading…