Hydrochloric Acid → HCID 1591231, compound

HRID 2090152Notes

Reaction equation

HRID 2090152 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][C:4]=1[OH:11].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+].C[C:25](P(OC)(O)=O)([C:27]([O-:29])=[O:28])C.[OH-].[Na+].Cl>CN1CCCC1=O.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:25]/[C:27]([OH:29])=[O:28])[CH:6]=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 1591231HCID 1591231, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5.00 g (32.86 mmol) Vanilin, 4.88 ml (39.48 mmol) n-pentylbromide and 13.62 g (98.59 mmol) potassium carbonate were dissolved in 50 ml 1-methyl-2-pyrrolidone. The reaction suspension was allowed to react for 6 hours at 25° C. Subsequently 8.55 ml (59.34 mmol) trimethylphosphonoacetate were added. The mixture was allowed to react for 18 hours at 25° C. Then 20 ml of a sodium hydroxide solution 28% in water were added. The reaction mixture was allowed to react for 1.5 hour at 70° C. After cooling, the mixture was acidified to pH=1 with hydrochloric acid 37 wt. %. The product was filtered off, washed with water and dried at 40° C. under vacuum to give 7.36 g (84.7%) (2E)-3-[3-methoxy-4-(pentyloxy)phenyl]prop-2-enoic acid as beige crystals.

Workup

  1. customto react for 6 hours at 25° C
  2. customto react for 18 hours at 25° C
  3. customto react for 1.5 hour at 70° C
  4. temperatureAfter cooling
  5. filtrationThe product was filtered off
  6. washwashed with water
  7. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-1deffa9048f94779b6dfe502415d4382
Source dataset
uspto-grants-2013_05
Patent number
US08436132B2

Reaction notes

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