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Sodium Hydroxide → 4-[[8-Acetyl-7-[3-(4-acetyl-3-hydroxypropylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid

HRID 465151
Notes
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Reaction equation

HRID 465151 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 540026604-[[8-Acetyl-7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester

Product 1

HCID 202327444-[[8-Acetyl-7-[3-(4-acetyl-3-hydroxypropylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperatureat reflux for an hour
  2. customThe methanol was removed in vacuo
  3. extractionThe precipitate was extracted with chloroform
  4. customdried
  5. customThe resulting semi-solid was purified by flash column chromatography (eluting with 2% methanol/ethylacetate)

Sources & evidence

ORD record
ord-4c19bcd1f2414210929c8d094fa714ca
Source dataset
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04550190

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes