Water → HCID 19809658, compound
Reaction equation
[CH3:1][C:2]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([CH3:27])=[CH:15][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10].[OH-].[K+].O>CO>[CH3:1][C:2]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:16]([CH3:27])=[CH:15][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([CH3:14])([CH3:13])[C:9]([OH:11])=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 7.8 g (2.1 mmol) of 5-[2,5-dimethyl-4-(phenylmethoxy)phenoxy]-2,2-dimethylpentanoic acid, methyl ester (Example 13), 3.5 g (3×21 mmol) of potassium hydroxide, 10 mL of water and 100 mL of methanol is stirred at reflux for 12 hours. The methanol is removed and the residual aqueous solution is diluted with 150 mL of water then back-extracted with diethyl ether. The aqueous layer is acidified with 15 mL of 6N hydrochloric acid solution and the product is isolated with diethyl ether. The diethyl ether solution is washed with brine, dried (magnesium sulfate) and evaporated leaving 6.9 g of a dark brown crystalline residue. Recrystallization from 30 mL of acetonitrile in the presence of charcoal affords 4.0 g of the title compound as tan, dense crystals; mp 104°-106° C.
Workup
- temperatureat reflux for 12 hours
- customThe methanol is removed
- additionthe residual aqueous solution is diluted with 150 mL of water
- extractionthen back-extracted with diethyl ether
- customthe product is isolated with diethyl ether
- washThe diethyl ether solution is washed with brine
- dry with materialdried (magnesium sulfate)
- customevaporated
Sources & evidence
- ORD record
- ord-9174f47edda043aab01b96934c4dbcfa
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166398
Reaction notes
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