Hydrochloric Acid → HCID 57747224, compound

HRID 1163462Notes

Reaction equation

HRID 1163462 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]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:27]([OH:36])=[C:26]([CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH:25]=1)=[O:23].Cl>C(OCC)(=O)C>[CH:30]1([C:28]2[CH:29]=[C:24]([C:22](=[O:23])[CH2:21][O:1][C:2]3[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=3[O:10][CH3:11])[CH:25]=[C:26]([CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]3)[C:27]=2[OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 87394924HCID 87394924, compound

Product 1

HCID 57747224HCID 57747224, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.52 g (10 mmol) of 4-hydroxy-3-methoxy-benzaldehyde, 0.3 g (2.0 mmol) of sodium iodide and 3.05 g (22 mmol) of potassium carbonate in 80 ml of ethyl acetate is stirred for 30 minutes. Then 3.8 g (10 mmol) of 2-bromo-1-(4-hydroxy-3,5-di-cyclohexylphenyl)-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/di-isopropylether yields 1.35 g of compound 103, m.p. 163-164° 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/di-isopropylether

Sources & evidence

ORD record
ord-782d8c623d8b433c83e1f9ae8f5df1fb
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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