Aluminium lithium hydride → HCID 178520956, compound

HRID 81088Notes

Reaction equation

HRID 81088 reaction equation
[C@H:1]1([C:11](OC)=[O:12])[CH2:6][CH2:5][C@H:4]([C:7](OC)=[O:8])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C@H:1]1([CH2:11][OH:12])[CH2:6][CH2:5][C@H:4]([CH2:7][OH:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178501164HCID 178501164, compound

Product 1

HCID 178520956HCID 178520956, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-dimethyl cyclohexane-1,4-dicarboxylate (1000 g, 5 mol) in THF (3000 mL) cooled to −20° C. was added LiAlH4 (570 g, 15 mol). The mixture was stirred at room temperature for 3 h, quenched with water (10 L), and filtered. The filtrate was concentrated in vacuo to give trans-cyclohexane-1,4-diyldimethanol as white solid. 1H NMR (CDCl3, 400 MHz): δ 3.48-3.46 (m, 4H), 1.86-1.84 (m, 4H), 1.47-1.42 (m, 4H), 1.01-0.96 (m, 4H).

Workup

  1. customquenched with water (10 L)
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-aa5517e5b96d4f2091a81b3648f01fa3
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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