o-Vanillin → HCID 69518044, compound

HRID 854919Notes

Reaction equation

HRID 854919 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:12][C:13]([F:22])([F:21])/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CS(C)=O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:3]2[C:2]=1[O:1][CH:14]([C:13]([F:12])([F:22])[F:21])[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4]2

Participants

4

Reactant 2

HCID 8991o-VanillinHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

Product 1

HCID 69518044HCID 69518044, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

The 2-hydroxy-3-methoxybenzaldehyde (3.05 g, 20mmol) was dissolved in DMSO (9 mL). TEA (4.09 g, 40 mmol) and ethyl 4,4,4-trifluorocrotonate (6.93 g, 40 mmol) were added to above solution. The reaction was heated to 70° C. and monitored by TLC and GCMS until done. The reaction was quenched with 10% HCl. The compound was extracted with EtOAc and washed with water and NH4Cl. The organic was dried over MgSO4. After concentrated, the crude compound was purified by flash column with 20% EtOAc in hexane. This ester was of suitable purity to use without further purification.

Workup

  1. customThe reaction was quenched with 10% HCl
  2. extractionThe compound was extracted with EtOAc
  3. washwashed with water and NH4Cl
  4. dry with materialThe organic was dried over MgSO4
  5. concentrationAfter concentrated
  6. customthe crude compound was purified by flash column with 20% EtOAc in hexane
  7. customto use without further purification

Sources & evidence

ORD record
ord-e3f6c8e4541842d4abf356300a533f51
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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