1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → 1-(Bis(4-methoxyphenyl)(phenyl)methoxy)icosan-3-ol

HRID 1886892Notes

Reaction equation

HRID 1886892 reaction equation
[CH2:1]([OH:22])[CH2:2][CH:3]([OH:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH3:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([C:29](Cl)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:27][CH:26]=1>N1C=CC=CC=1>[CH3:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([C:29]([C:28]2[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:22][CH2:1][CH2:2][CH:3]([OH:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 25229601Icosane-1,3-diol

Product 1

HCID 687487641-(Bis(4-methoxyphenyl)(phenyl)methoxy)icosan-3-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Icosane-1,3-diol (3.7 g, 11.8 mmoles) is co-evaporated twice with anhydrous pyridine (50 mL each) and then is dissolved in anhydrous pyridine (60 mL). The solution is chilled in an ice bath, and 4,4′-dimethoxytritylchloride (4.2 g, 12.4 mmoles) is added. The reaction is allowed to warm to ambient temperature and is stirred for 16 hours. The remaining 4,4′-dimethoxytritylchloride is quenched with methanol (10 mL), and the yellow solution is then evaporated to near dryness. The residue is co-evaporated twice to dryness with toluene (50 mL each). The crude product is purified on silica gel (150 mL bed volume) eluting with hexanes:acetone:triethylamine (95.5:5:0:5 [v/v/v], 500 mL). Fractions containing pure product by thin layer chromatography are pooled and evaporated to a pale yellow syrup. The syrup is dried well in vacuo. The yield is 6.8 g (93%).

Workup

  1. temperatureThe solution is chilled in an ice bath
  2. customThe remaining 4,4′-dimethoxytritylchloride is quenched with methanol (10 mL)
  3. customthe yellow solution is then evaporated
  4. customThe crude product is purified on silica gel (150 mL bed volume)
  5. washeluting with hexanes:acetone:triethylamine (95.5:5:0:5 [v/v/v], 500 mL)
  6. additionFractions containing pure product by thin layer chromatography
  7. customevaporated to a pale yellow syrup
  8. customThe syrup is dried well in vacuo

Sources & evidence

ORD record
ord-52688e021b1e46708b0afc774d76c488
Source dataset
uspto-grants-2013_08
Patent number
US08501706B2

Reaction notes

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