Hydrochloric Acid → HCID 54142924, compound

HRID 615512Notes

Reaction equation

HRID 615512 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].Br[CH2:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.CC(C)=O>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH2:16][CH2:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=1[OH:10])(=[O:12])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1040684-(2-Bromoethyl)benzoic acidHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 54142924HCID 54142924, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 1 g (5.55 mmoles) of 2,4-dihydroxy-3-propylacetophenone, 1.27 g (5.55 mmoles) of para-(β-bromoethyl)benzoic acid, 2.4 g of potassium carbonate, and 50 ml of dry acetone was stirred and refluxed for 3 days. The reaction flask was cooled and the stirred mixture was diluted with H2O and acidified with 6N HCl. Extraction with ethyl acetate and drying with Na2SO4 afforded the crude product after evaporating the ethyl acetate in vacuo. Pure 4-β-(4-acetyl-3-hydroxy-2-propylphenoxy)ethyl benzoic acid was isolated by flash chromatography on silica gel eluting with 5% MeOH/CH2Cl2 containing 0.1% acetic acid.

Workup

  1. temperaturerefluxed for 3 days
  2. temperatureThe reaction flask was cooled
  3. extractionExtraction with ethyl acetate
  4. dry with materialdrying with Na2SO4
  5. customafforded the crude product
  6. customafter evaporating the ethyl acetate in vacuo

Sources & evidence

ORD record
ord-8400b4c12315465fac144030d667f7df
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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