Hydrochloric Acid → HCID 21837911, compound
Reaction equation
C([O:3][C:4](=[O:27])[C:5]([Cl:26])([Cl:25])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)C.[OH-].[K+].Cl>C(O)C>[Cl:26][C:5]([Cl:25])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:4]([OH:27])=[O:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3.50 g (16.3 mmol) 89 was reacted analogously to example 27 with 5.2 g (16.3 mmol) of the ethyl ester of 7. 5.2 g (70%) 2,2-dichloro-8-[5-(4-chlorophenyl)-pentyl-sulfenyl]-octanoic acid ethyl ester 86 was obtained as a colourless oil after flash chromatography (heptanel toluene 2:1). 2.5 g (5.5 mmol) 86, 11 ml (11 mmol) 1 N KOH and 11 ml ethanol were stirred for 2 h at room temperature. It was acidified with 2 N HCl to pH 2 while cooling in an ice-bath, ethanol was removed by distillation, it was extracted with ether, washed with water, dried over Na2SO4 and, after removing the solvent, 2.24 g (96%) 34 was obtained as a colourless oil. 1.14 g (78%) of the sodium salt of 34 with a melting point of 154° C. was obtained from 1.41 g (3.29 mmol) 34 in 3 ml ethanol and 0.13 g (3.3 mmol) sodium hydroxide in 5 ml ethanol after mixing, admixing with ether, suction filtering and drying.
Workup
- temperaturewhile cooling in an ice-bath
- customethanol was removed by distillation, it
- extractionwas extracted with ether
- washwashed with water
- dry with materialdried over Na2SO4
- customafter removing the solvent
Sources & evidence
- ORD record
- ord-94263a66e5f14ab99ec5aeaeb9f001d5
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05968982
Reaction notes
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