Acetone → HCID 70486976, compound

HRID 2164958Notes

Reaction equation

HRID 2164958 reaction equation
C(OC(=O)[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25]Br)[C:10]=1[CH2:27][CH2:28][CH3:29])C.[OH:31][C:32]1[C:37]([CH2:38][CH2:39][CH3:40])=[C:36]([OH:41])[CH:35]=[CH:34][C:33]=1[C:42](=[O:44])[CH3:43].[C:45](=[O:48])([O-])[O-:46].[K+].[K+].[CH3:51][C:52](C)=O>CN(C)C=O>[CH2:51]([O:46][C:45](=[O:48])[CH:7]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][O:41][C:36]2[CH:35]=[CH:34][C:33]([C:42](=[O:44])[CH3:43])=[C:32]([OH:31])[C:37]=2[CH2:38][CH2:39][CH3:40])[C:10]=1[CH2:27][CH2:28][CH3:29])[CH2:6][CH3:5])[CH3:52]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 14330015HCID 14330015, compound

Product 1

HCID 70486976HCID 70486976, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.13 g (0.0044 mole) of 4-[4-acetyl-3-[3-(3-bromopropoxy)propoxy]-2-propylphenoxy]butanoic acid ethyl ester, 0.85 g (0.0044 mole) of 1-(2,4-dihydroxy-3-propylphenyl)ethanone and 1.2 g (0.0087 mole) of potassium carbonate in 40 ml of anhydrous acetone and 20 ml of anhydrous dimethylformamide was stirred at reflux for 20 hours. The solvents were removed in vacuo and the residue was purified by HPLC using 35% ethyl acetate-hexane to give 2.15 g (82% yield) of [4-acetyl-3-[3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]propoxy]-2-propylphenoxy]butanoic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 20 hours
  2. customThe solvents were removed in vacuo
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-ef4c11d2875a4f5a86b45cf5f0044138
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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