4-Methyloxybenzyl chloride → 1,1'-[Oxybis(methylene)]bis(4-methoxybenzene)

HRID 651544Notes

Reaction equation

HRID 651544 reaction equation
CC1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/[CH2:18][OH:19].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1.C[C:33]1[CH:49]=[CH:48][C:47](C)=[CH:46][C:34]=1[CH2:35][O:36]CC1C=C(C)C=CC=1C>>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][O:36][CH2:35][C:34]2[CH:46]=[CH:47][C:48]([O:19][CH3:18])=[CH:49][CH:33]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 445354RetinolHCID 22111392HCID 22111392, compound

Product 1

HCID 2211761,1'-[Oxybis(methylene)]bis(4-methoxybenzene)

Procedure

Retinyl 4-Methoxybenzyl Ether (3e) was prepared from retinol and 4-methoxybenzyl chloride by the method described for 3c. The ether extract was washed successively with saturated sodium bicarbonate solution and with brine. The crude product was purified by successive chromatographic operations with the column absorbent and eluting solvent as follows: deactivated alumina, pentane and then 95:5 pentane-ethyl acetate; silica gel 60, chloroform; silica gel 60, 4:1 chloroform-pentane; repetition of the last method. The purified product was a yellow syrup: HPLC, 99.3% (340 nm), 100% (254 nm); MS m/z 406 (M), 285 (C20H29O), 269 (C20H29), 255 (C19H27), 121 (4-methoxybenzyl); UV λmax326 nm (ε 51 300), 226 nm (ε 14 000); 1H NMR (CDCl3) δ 7.27 (m, 2H, H2′), 6.88 (m, 2H, H3′), 6.59(dd, 1H, H11, J10,11=11.3 Hz, J11,12=15.0Hz), 6.29 (d, 1H, H12), 6.15 (bd, 1H, H8,J7,8=16.0Hz), 6.11 (d, 1H, H7), 6.09 (d, 11H, H10), 5.68 (t, 1H, H14), 4.45 (s, 2H, H21), 4.15 (d, 2H, H15, J14,15=6.8 Hz), 3.80 (s, 3H, OCH3), 2.01 (t, 2H, H4), 1.95 (s, 3H, H17), 1.82 (s, 3H, H20), 1.71 (s, 3H, H18), 1.65-1.57 (m, 2H, H3), 1.48-1.44 (m, 3H, H2), 1.02 (s, 6H, H16, H17). Anal. Calcd. for C28H38O2.½H2O:C, 80.92; H, 9.46. Found: C, 80.93; H, 9.38.

Workup

  1. extractionThe ether extract
  2. washwas washed successively with saturated sodium bicarbonate solution and with brine
  3. customThe crude product was purified by successive chromatographic operations with the column absorbent
  4. washeluting solvent

Sources & evidence

ORD record
ord-a214524a47ff44bea3539b9597f357b6
Source dataset
uspto-grants-2001_08
Patent number
US06281250B1

Reaction notes

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