Sodium Hydroxide → 4-[[8-Acetyl-7-[3-(4-acetyl-3-hydroxypropylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid
Reaction equation
C[O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:36](=[O:38])[CH3:37])[C:12]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25](O)[C:24]=3[CH2:33][CH2:34][CH3:35])=[CH:13][CH:14]=2)[CH:9]=1.[OH-:40].[Na+]>CO>[C:36]([C:11]1[C:12]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][C:24]=2[CH2:33][CH2:34][CH2:35][OH:40])=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[C:8]([O:7][CH2:6][CH2:5][CH2:4][C:3]([OH:2])=[O:39])[CH:17]=[CH:16]2)(=[O:38])[CH3:37]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1.44 g of 4-[[8-acetyl-7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester and 27 ml of 1N sodium hydroxide in 54 ml of methanol was stirred at reflux for an hour. The methanol was removed in vacuo and the clear solution was acidified to pH 3. The precipitate was extracted with chloroform and dried. The resulting semi-solid was purified by flash column chromatography (eluting with 2% methanol/ethylacetate) to yield 0.9 g (64%) of 4-[[8-Acetyl-7-[3-(4-acetyl-3-hydroxypropylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid of mp 121°-124°.
Workup
- temperatureat reflux for an hour
- customThe methanol was removed in vacuo
- extractionThe precipitate was extracted with chloroform
- customdried
- customThe resulting semi-solid was purified by flash column chromatography (eluting with 2% methanol/ethylacetate)
Sources & evidence
- ORD record
- ord-5c29d56874334872a7ab061e24bbd7c0
- Source dataset
- uspto-grants-1986_10
- Patent number
- US04616091
Reaction notes
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