Aluminium lithium hydride → [5-(Hexadecyloxy)-1,3-phenylene]dimethanol

HRID 874707Notes

Reaction equation

HRID 874707 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:11]=[C:6]([C:7](OC)=[O:8])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:15]([O:14][C:12]1[CH:11]=[C:6]([CH2:7][OH:8])[CH:5]=[C:4]([CH2:3][OH:2])[CH:13]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58947033HCID 58947033, compound

Product 1

HCID 58793317[5-(Hexadecyloxy)-1,3-phenylene]dimethanolYield 37.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product was generated using general protocol E using dimethyl-5-hexadecyloxyisophthalate (D10, 6.30 g), lithium aluminum hydride (1.27 g, 33.5 mmol), Et2O (150 mL) yielded 2.06 g (37.9%) of a white solid. 1H NMR (CDCl3, 400 MHz) δ: 6.93 (s, 1H, Ar—H), 6.85 (s, 2H, Ar—H), 4.67 (d, 3J=5.9 Hz, 4H, Ar—CH2—OH), 3.97 (t, 6.4 Hz, 2H, O—CH2), 1.78 (p, 3J=7.6 Hz, 2H, OCH2CH2), 1.66 (t, 3J=6.0 Hz, 2H, CH2—OH), 1.45 (p, 3J=7.6 Hz, 2H, O CH2CH2CH2), 1.26 (m, 24H), 0.88 (t, 3J=6.6, 3H, CH2—CH3).

Sources & evidence

ORD record
ord-165e7a73c62945ff936d9e7222c48eaf
Source dataset
uspto-grants-2015_03
Patent number
US08980925B2

Reaction notes

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