Hydroquinone → HCID 11011196, compound
Reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]1([CH:14]=[CH:13][C:11]([OH:12])=[CH:10][CH:9]=1)O.I[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21]>CN(C=O)C>[CH2:16]([O:12][C:11]1[CH:13]=[CH:14][C:7]([O:4][CH2:1][CH2:13][CH2:14][CH2:7][CH:9]=[CH2:10])=[CH:9][CH:10]=1)[CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a 60 mL DMF suspension of potassium carbonate (3.98 g, 28.8 mmol) were added hydroquinone (1.05 g, 9.54 mmol) and 6-iodo-1-hexene (6.01 g, 28.6 mmol) at room temperature. The reaction mixture was warmed to 100° C. and stirred for 10 h. After cooling to room temperature, the mixture was quenched with 10% aqueous sodium hydroxide (60 mL). The mixture was extracted with diethyl ether (3×50 mL). The combined organic solutions were washed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The crude product was purified by MPLC (80:1, hexane:ethyl acetate) to give the olefin 10 (1.86 g, 71%) as a white solid (mp=29.0°-30.0° C.); Anal. Calcd for C18H26O2 : C, 78.79%; H, 9.55%. Found: C, 78.69%; H, 9.37%; cap gc: tR =10.49 min; column: 25 m×0.25 mm, OV-101;temp prog: 50° C./4 min/20° C. min-1 /250° C./0 min; tlc: Rf =0.48 in 9:1 hexane:ethyl acetate.
Workup
- temperatureAfter cooling to room temperature
- customthe mixture was quenched with 10% aqueous sodium hydroxide (60 mL)
- extractionThe mixture was extracted with diethyl ether (3×50 mL)
- washThe combined organic solutions were washed with aqueous saturated sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe crude product was purified by MPLC (80:1, hexane:ethyl acetate)
Sources & evidence
- ORD record
- ord-0ceefc08fccc4420a5931dd6d7f301b0
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05677467
Reaction notes
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