Water → 4-(2-Hydroxyethyl)cyclohexan-1-ol

HRID 1524758Notes

Reaction equation

HRID 1524758 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1.[AlH4-].[Li+].O.[OH-].[Na+]>CCOCC.C1COCC1>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1

Participants

7

Conditions

Temperature
0 °C

Procedure

4-(2-Hydroxyethyl)cyclohexanone (2.00 g, 0.0141 mol) was dissolved in ether (30.00 mL) and was cooled at 0° C. To the reaction was added 1.0 M lithium tetrahydroaluminate in ether (14.1 mL) and the resulting mixture was stirred at 0° C. for 2 hours and at 25° C. for 16 hours. To the reaction was added THF (20.00 mL) and this mixture was cooled at 0° C. and then water (0.40 mL, 0.022 mol) was added, followed by 1.00 M sodium hydroxide (0.40 mL). To the reaction was then added ether (100.00 mL) and the resulting mixture was stirred for 10 minutes, then was filtered and the filtrate was concentrated using a rotary evaporator to provide the crude product. The crude product was used in the next reaction without further purification.

Workup

  1. temperaturethis mixture was cooled at 0° C.
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-b85d8708978f4c73b8010af68dc4858c
Source dataset
uspto-grants-2015_07
Patent number
US09079912B2

Reaction notes

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