Aluminium lithium hydride → [1-(Hydroxymethyl)-4,4-dimethoxycyclohexyl]methanol

HRID 1855025Notes

Reaction equation

HRID 1855025 reaction equation
[CH3:1][O:2][C:3]1([O:18][CH3:19])[CH2:8][CH2:7][C:6]([C:14](OC)=[O:15])([C:9](OCC)=[O:10])[CH2:5][CH2:4]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.C1COCC1>[CH3:19][O:18][C:3]1([O:2][CH3:1])[CH2:4][CH2:5][C:6]([CH2:9][OH:10])([CH2:14][OH:15])[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 904099121-Ethyl 1-methyl 4,4-dimethoxycyclohexane-1,1-dicarboxylate

Product 1

HCID 90408533[1-(Hydroxymethyl)-4,4-dimethoxycyclohexyl]methanolYield 102.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-ethyl 1-methyl 4,4-dimethoxycyclohexane-1,1-dicarboxylate (4.7 g, 17.13 mmol) in dry Et2O (250 mL) at 0° C. was added LiAlH4 (17.1 mL of a 2 M solution in THF; 34.3 mmol) dropwise over 15 min. The reaction mixture was stirred at 0° C. for 15 min, then warmed to rt and stirred for 1 h. It was then cooled to 0° C. and carefully quenched with aqueous NaOH (7.3 mL of a 1N solution; 7.3 mmol). The mixture was filtered and the filtrate was concentrated in vacuo to afford the title compound (3.6 g, 100% yield) as a semisolid. 1H NMR (500 MHz, CDCl3) δ 3.65 (d, J=4.4 Hz, 4H), 3.20 (s, 6H), 2.42 (t, J=4.6 Hz, 2H), 1.67 (dd, J=7.3, 4.9 Hz, 4H), 1.53-1.41 (m, 4H).

Workup

  1. temperaturewarmed to rt
  2. stirringstirred for 1 h
  3. temperatureIt was then cooled to 0° C.
  4. customcarefully quenched with aqueous NaOH (7.3 mL of a 1N solution
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-70d387a010b7460f841b4e4f715b3ba6
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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