Diethyl Ether → 2,5-Bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde

HRID 1528560Notes

Reaction equation

HRID 1528560 reaction equation
CC1C2N=[C:9]([C:11]3[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:14]([CH2:24][OH:25])=[CH:13][C:12]=3[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[O:10]C=2C=CC=1.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](Cl)([O-])(=O)=O.CCOCC>C(Cl)Cl>[CH2:27]([O:26][C:12]1[CH:13]=[C:14]([CH2:24][OH:25])[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:11]=1[CH:9]=[O:10])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 867124912-(4-Methylbenzoxazolyl)-5-(hydroxylmethyl)-1,4-bis(hexyloxy)benzeneHCID 178479088HCID 178479088, compound

Product 1

HCID 867124922,5-Bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-methylbenzoxazolyl)-5-(hydroxylmethyl)-1,4-bis(hexyloxy)benzene (1.99 g, 4.53 mmol) in CH2Cl2 (10 mL) was added dropwise to a stirred solution of freshly prepared pyridium chlorochromate (PCC) (1.46 g, 6.80 mmol) in CH2Cl2 (100 mL) at room temperature. Anhydrous Et2O (100 mL) was added, and the mixture was stirred for an additional 2 h. The reaction mixture was then directly transferred onto the top of a short silica gel column. The yellow and highly fluorescent product was then washed off the column with CH2Cl2, giving 2,5-bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde in 86.9% (1.72 g). The product (mp. 48-50° C.) had the following spectral properties. 1H NMR (CDCl3, 300 MHz, δ): 10.53 (s, 1H, —CHO), 7.78 (s, 1H), 7.48 (s, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.26 (dd, J=7.8 Hz, J=7.8 Hz, 1H), 7.17 (d, J=7.2 Hz, 1H), 4.18 (t, J=6.6 Hz, 2H), 4.12 (t, J=6.0 Hz, 2H), 2.68 (s, 3H), 1.87 (q, J=6.3 Hz, 4H), 1.54 (m, 4H), 1.35 (m, 8H), 0.90 (m, 6H). IR(KBr): 1684 cm−1, 1609.5 cm−1, 1534.6 cm−1.

Workup

  1. washThe yellow and highly fluorescent product was then washed off the column with CH2Cl2

Sources & evidence

ORD record
ord-d0966c7f4ae44c7cbeecfb65c30c6858
Source dataset
uspto-grants-2015_07
Patent number
US09090602B2

Reaction notes

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