Ethanol → HCID 14078297, compound
Reaction equation
[CH2:1]1[CH2:12][O:11][C:3]([CH3:10])([CH2:4][CH2:5][CH2:6][C:7]([CH3:9])=[CH2:8])[O:2]1.C([OH:15])C.[OH-].[Na+].OO>CCCCCC>[CH2:12]1[CH2:1][O:2][C:3]([CH3:10])([CH2:4][CH2:5][CH2:6][CH:7]([CH3:9])[CH2:8][OH:15])[O:11]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6,6-ethylenedioxy-2-methyl-hept-1-ene (33.95 g) in hexane (132 ml) under a nitrogen atmosphere is added borane-methyl sulfide complex (7.05 ml) at 0° C. over a half hour period. The reaction is allowed to stir for 3 hours at room temperature and is treated with 95% ethanol (68 ml) and 3N sodium hydroxide (21.8 ml), cooled to 0° C., followed by the dropwise addition of 30% hydrogen peroxide (24.5 ml) to maintain a temperature of 25°-35° C. The reaction mixture is heated at reflux for one half hour, poured into ice water (500 ml) and partitioned between ether and water. The aqueous phase is extracted with ether and the combined extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give 6,6-ethylenedioxy-2-methyl-heptanol (33.35 g, 89%): nmr (CDCl3,δ), 0.93 (d, 3H, CH3CH<), 1.32 ##STR11## 3.45 (bd, 2H, CHCH2O), 3.93 (s, 5H, OCH2CH2O and CH3CH<).
Workup
- temperaturecooled to 0° C.
- temperatureto maintain a temperature of 25°-35° C
- temperatureThe reaction mixture is heated
- temperatureat reflux for one half hour
- custompartitioned between ether and water
- extractionThe aqueous phase is extracted with ether
- washthe combined extracts are washed with brine
- dry with materialdried (Na2SO4)
- customThe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-65b5ea1b5f1341ffa86dd3672a09d376
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04237055
Reaction notes
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