Aluminium lithium hydride → (3,5-dimethoxy-4-propan-2-yl-phenyl)methanol

HRID 450904Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:22][CH3:23])[C:18]=1[CH:19]([CH3:21])[CH3:20])[C:12](OC)=[O:13]>CCOCC>[CH3:23][O:22][C:17]1[CH:16]=[C:11]([CH:10]=[C:9]([O:8][CH3:7])[C:18]=1[CH:19]([CH3:21])[CH3:20])[CH2:12][OH:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of LiAlH4 (95%) (5.00 g, 125 mmol) in dry ether (100 mL) at 0° C. was added a solution of methyl 3,5-dimethoxy-4-i-propylbenzoate (17.67 g, 90.1 mmol), obtained in example 1(b) in ether (300 mL) under N2. The suspension was stirred at 0° C. for one hour then for an additional hour at room temperature. The reaction was quenched by slow addition of a saturated Na2SO4 aqueous solution (10 mL) at 0° C. The mixture was stirred overnight. The solid was filtered off and the filtrate was evaporated to dryness to give 3,5-dimethoxy-4-i-propylbenzyl alcohol (13.76 g, 88.3% yield) as white crystals. 1HNMR (CDCl3, ppm): δ 1.34 (d, J=7.2 Hz, 6H), 3.65 (hept., J=7.2 Hz, 1H), 3.88 (s, 6H), 4.70 (s, 2H), 6.62 (s, 2H).

Workup

waitfor an additional hour at room temperature
customThe reaction was quenched by slow addition of a saturated Na2SO4 aqueous solution (10 mL) at 0° C
stirringThe mixture was stirred overnight
filtrationThe solid was filtered off
customthe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-0f6ffc06ded2443b8d1dfb8ca6f2af11
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487009B2

Reaction notes

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