[4-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid ethyl ester → [4-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid
Reaction equation
C([O:3][C:4](=[O:37])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([OH:30])[C:22]=2[CH2:31][CH2:32][CH3:33])[C:8]=1[CH2:34][CH2:35][CH3:36])C>C(O)C.[OH-].[Na+]>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:37])=[O:3])=[C:8]([CH2:34][CH2:35][CH3:36])[C:9]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([OH:30])[C:22]=1[CH2:31][CH2:32][CH3:33])(=[O:15])[CH3:14]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 1.94 g of [4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid ethyl ester in 5 ml of ethanol and 20 ml of 1.0N sodium hydroxide was refluxed for 1 hour. After cooling, ice water was added and the mixture was acidified. The precipitate was extracted with methylene chloride. The dried, over magnesium sulfate, extract was concentrated in vacuo to an oil. Crystallization from ether-hexane gave 1.29 g, mp 124°-125°, (71% yield) of [4-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid.
Workup
- temperaturewas refluxed for 1 hour
- temperatureAfter cooling
- extractionThe precipitate was extracted with methylene chloride
- extractionThe dried, over magnesium sulfate, extract
- concentrationwas concentrated in vacuo to an oil
- customCrystallization from ether-hexane
Sources & evidence
- ORD record
- ord-22a5865a0cab4ea391f33686d999af0f
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04782176
Reaction notes
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