Hydrochloric Acid → HCID 86631893, compound

HRID 1163461Notes

Reaction equation

HRID 1163461 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8]([OH:14])=[C:7]([CH:15]([CH3:17])[CH3:16])[CH:6]=1)=[O:4].[OH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=1[O:27][CH3:28].C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>O>[CH:15]([C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][C:20]=2[O:27][CH3:28])[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[C:8]=1[OH:14])([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1183VanillinHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 53782490HCID 53782490, compound

Product 1

HCID 86631893HCID 86631893, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6.00 g (18.3 mmol) of 2-bromo-1-(4-hydroxy-3,5-di-isopropylphenyl)-ethanone and 2.78 g (18.3 mmol) of 4-hydroxy-3-methoxy-benzaldehyde in 20 ml of ethyl acetate 5.00 g (36.7 mmol) of potassium carbonate is added and the mixture is stirred for 18 hours at room temperature. After addition of water and adjusting the pH to 5-6 by adding 32% HCl, the mixture is extracted with ethyl acetate. The combined extracts are washed with water, dried and evaporated to give compound 102. 1H-NMR (300 MHz, CDCl3), δ (ppm): 7.79 (s, 2H), 7.46-7.45 (d, 1H), 7.41-7.38 (dd, 1H), 6.90-6.87 (d, 1H), 5.43 (s, 2H), 3.97 (s, 3H), 3.24-3.15 (sept., 2H), 1.32-1.29 (d, 12H).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe combined extracts are washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-dd6ed78bc1fc49899371abb61faad069
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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