Hydrochloric Acid → HCID 57747235, compound

HRID 1163466Notes

Reaction equation

HRID 1163466 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]([C:25]1[CH:26]=[C:27]([C:37](=[O:40])[CH2:38]Br)[CH:28]=[C:29]([C:32]([CH3:36])([CH3:35])[CH2:33][CH3:34])[C:30]=1[OH:31])([CH3:24])[CH2:22][CH3:23].Cl>C(OCC)(=O)C>[CH3:24][C:21]([C:25]1[CH:26]=[C:27]([C:37](=[O:40])[CH2:38][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=2[O:10][CH3:11])[CH:28]=[C:29]([C:32]([CH3:36])([CH3:35])[CH2:33][CH3:34])[C:30]=1[OH:31])([CH3:20])[CH2:22][CH3:23]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 86631892HCID 86631892, compound

Product 1

HCID 57747235HCID 57747235, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.55 g (10 mmol) of 4-hydroxy-3-methoxy-benzaldehyde, 0.30 g (2.0 mmol) of sodium iodide and 3.05 g (22 mmol) of potassium carbonate in 100 ml of ethyl acetate is stirred for 30 minutes. Then 3.56 g (10 mmol) of 1-[3,5-bis(1,1-dimethyl-propyl)-4-hydroxy-phenyl]-2-bromo-ethanone is added and stirring at room temperature is continued for 16 hours. Then the mixture is acidified with 2N HCl and extracted with ethyl acetate. The combined extracts are washed with water, dried and evaporated. Crystallization of the crude product from hexane yields 2.95 g (69%) of compound 107, m.p. 106-107° C.

Workup

  1. stirringstirring at room temperature
  2. waitis continued for 16 hours
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts are washed with water
  5. customdried
  6. customevaporated
  7. customCrystallization of the crude product from hexane

Sources & evidence

ORD record
ord-e703b4826e35479f8521991766c80267
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

Loading…