tert-Butanol → 86023-87-2

HRID 1585533Notes

Reaction equation

HRID 1585533 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. temperaturecooled to room temperature
  4. customreaction

Sources & evidence

ORD record
ord-ba9629a5c78d4b599847c0508d30ec4f
Source dataset
uspto-grants-1999_08
Patent number
US05939398

Reaction notes

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