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

HRID 40982
Notes
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Reaction equation

HRID 40982 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 157003924-(2-Hydroxyethyl)cyclohexan-1-one

Product 1

HCID 137511534-(2-Hydroxyethyl)cyclohexan-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
3×
HCID 8028TetrahydrofuranSolvent

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-80fda129872c4577b0185fdb7b5229dc
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530485B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes