HCID 12361490, compound → HCID 67507886, compound

HRID 874705Notes

Reaction equation

HRID 874705 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][CH3:28])[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][CH3:28]

Participants

4

Reactant 2

HCID 12361490HCID 12361490, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 67507886HCID 67507886, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product was generated using general protocol E using dimethyl-5-tetradecyloxyisophthalate (D9, 1.171 g, 2.88 mmol), lithium aluminum hydride (0.253 g, 6.34 mmol), Et2O (40 mL) yielded 0.538 g (53.3%) of a white solid. 1H NMR (CDCl3, 300 MHz) δ: 6.9336 (s, 1H, Ar—H), 6.8501 (s, 2H, Ar—H), 4.6821 (s, 4H, Ar—CH2), 3.9708 (t, 2H, O—CH2, 3J=6.58 Hz), 1.7784 (p, 2H, O—CH2—CH2, 3J=7.16 Hz), 1.6328 (t, 2H, O—H), 1.4483 (p, 2H, O—CH2—CH2—CH2, 3J=7.58 Hz), 1.2625 (m, 20H), 0.8810 (t, 3H, CH2—CH3, 3J=6.83 Hz).

Sources & evidence

ORD record
ord-d99fed425b834300bbefce7c07e5a74b
Source dataset
uspto-grants-2015_03
Patent number
US08980925B2

Reaction notes

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