Ethyl 4-oxocyclohexanecarboxylate → Rac-(1s,4s)-4-(hydroxymethyl)cyclohexanol

HRID 2289174Notes

Reaction equation

HRID 2289174 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8](OCC)=[O:9])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:9][CH2:8][CH:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12892866Rac-(1s,4s)-4-(hydroxymethyl)cyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-oxocyclohexanecarboxylate (Aldrich Chemical Co., Milwaukee, Wis.) is reduced with excess lithium aluminum hydride in tetrahydrofuran to provide 4-(hydroxymethyl)cylohexan-1-ol.

Sources & evidence

ORD record
ord-0f9239c37cbc4506a28348a60dc29198
Source dataset
uspto-grants-2000_07
Patent number
US06090950

Reaction notes

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