tert-Butanol → 86023-87-2

HRID 1941180Notes

Reaction equation

HRID 1941180 reaction equation
Br[C@H:2]1[C:28](=[O:29])[C@@:27]2([CH3:30])[C@@H:13]([CH2:14][C@@H:15]3[O:20][C@@:19]4([O:26][CH2:25][C@H:23]([CH3:24])[CH2:22][CH2:21]4)[C@@H:17]([CH3:18])[C@@H:16]32)[C@H:12]2[C@H:3]1[C@:4]1([CH3:32])[C@@H:9]([CH2:10][CH2:11]2)[CH2:8][C@@H:7]([OH:31])[CH2:6][CH2:5]1.C([OH:37])(C)(C)C.[OH-].[Na+]>O>[CH3:18][C@@H:17]1[C@:19]2([O:26][CH2:25][C@H:23]([CH3:24])[CH2:22][CH2:21]2)[O:20][C@H:15]2[CH2:14][C@@H:13]3[C@@:27]([CH3:30])([C@@H:16]12)[C@H:28]([OH:29])[C:2](=[O:37])[C@H:3]1[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@:4]1([CH3:32])[CH2:5][CH2:6][C@H:7]([OH:31])[CH2:8]2

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 10673254HCID 10673254, compound

Product 1

HCID 15891086023-87-2

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
83 °C

Procedure

A glass lined reactor was charged with 12.4 Kg of (3β,5α,11β,25R)-11-bromospirostan-3-ol-12-one (24.34 mole), 33 gallons of t-butanol, 33 gallons of water and 7.5 Kg (189 mole, 7.75 eq) of sodium hydroxide pellets. The reaction was heated to reflux over 1.5 hours, maintained at reflux for 4.5 hours (pot temperature was 83° C.), then cooled to room temperature. TLC at this point indicated complete reaction.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux over 1.5 hours
  3. temperaturemaintained
  4. temperaturecooled to room temperature
  5. customreaction

Sources & evidence

ORD record
ord-27d33e0bf4c940a1bf0b7580e434818d
Source dataset
uspto-grants-1997_12
Patent number
US05703052

Reaction notes

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