Ethanol → HCID 53672878, compound
Reaction equation
[CH2:1]([O:3][C:4](=[S:22])[CH:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])[CH3:2].C(O)C.[OH-].[Na+]>O>[CH2:1]([O:3][C:4](=[S:22])[CH:5]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred, ice-cold solution of 20.4 g. of diethyl-2-phenylthio-1,8-octanedioate in 100 ml. of ethanol is added dropwise a solution of 2.41 g. of sodium hydroxide in 12 ml. of water during 5 minutes. The resulting solution is maintained at 0° C. for 3.5 days and then at ambient temperature for 2 hours. The bulk of the ethanol is removed in vacuo and the residue is partitioned with ether and water. The aqueous layer is acidified with dilute hydrochloric acid and the acidic materials are extracted with ether. This extract is washed with water and brine, dried and concentrated. The residue is subjected to dry column chromatography on silica gel with 30:20:1 ethyl acetate-heptane-acetic acid providing the product as a light yellow oil. Its infra-red spectrum has peaks at 1735 and 1700 cm-1.
Workup
- customThe bulk of the ethanol is removed in vacuo
- customthe residue is partitioned with ether and water
- extractionthe acidic materials are extracted with ether
- washThis extract is washed with water and brine
- customdried
- concentrationconcentrated
- dry with materialto dry column chromatography on silica gel with 30:20:1 ethyl acetate-heptane-acetic acid providing the product as a light yellow oil
Sources & evidence
- ORD record
- ord-213f3a5898e34359af45a63cc274f585
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04644079
Reaction notes
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