Hydrochloric Acid → HCID 57747234, compound

HRID 1163460Notes

Reaction equation

HRID 1163460 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+].Br[CH2:21][C:22]([C:24]1[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:27]([OH:34])=[C:26]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:25]=1)=[O:23].Cl>C(OCC)(=O)C>[C:30]([C:28]1[CH:29]=[C:24]([C:22](=[O:23])[CH2:21][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:25]=[C:26]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:27]=1[OH:34])([CH3:33])([CH3:31])[CH3:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one

Product 1

HCID 57747234HCID 57747234, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 19.4 g (125 mmol) of 4-hydroxy-3-methoxy-benzaldehyde, 1.88 g (12.5 mmol) of sodium iodide and 34.5 g (250 mmol) of potassium carbonate in 1000 ml of ethyl acetate is stirred for 30 minutes. Then 43.6 g (125 mmol) of 2-bromo-1-(4-hydroxy-3,5-di-tert-butylphenyl)-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 dichloro-methane/hexane yields 36.85 g of compound 101, m.p. 99-100° 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 dichloro-methane/hexane

Sources & evidence

ORD record
ord-c1cbc61ae17f4452994951b4e311447c
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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