1,6-Hexanediol → 6-(Bis(4-methoxyphenyl)phenylmethoxy)-1-hexanol

HRID 37031

Reaction equation

HRID 37031 reaction equation
[C:1](Cl)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:10]1[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[CH:12][CH:11]=1)[C:2]1[CH:9]=[CH:8][C:5]([O:6][CH3:7])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH2:34]([OH:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][OH:40]>N1C=CC=CC=1>[CH3:7][O:6][C:5]1[CH:8]=[CH:9][C:2]([C:1]([O:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][OH:41])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]2[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 123741,6-HexanediolHCID 81531DiisopropylethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 6275066-(Bis(4-methoxyphenyl)phenylmethoxy)-1-hexanolYield 33.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.38 g (10 mmol) of DMTr-Cl and 3.45 mL (20 mmol) of diisopropylethylamine in 50 mL of dry pyridine was added 5.91 g (50 mmol) of 1,6-hexanediol. After stirring for 4 h, the mixture was quenched with 85 mL of 5% sodium bicarbonate and extracted with 2×100 mL of methylene chloride. The organic phase was washed with 2×100 mL of water and 100 mL of brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (3.5×17 cm silica) using methylene chloride. The fractions containing pure product were combined and concentrated to give 1.40 g of 37 as a yellow syrup.

Workup

  1. customthe mixture was quenched with 85 mL of 5% sodium bicarbonate
  2. extractionextracted with 2×100 mL of methylene chloride
  3. washThe organic phase was washed with 2×100 mL of water and 100 mL of brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (3.5×17 cm silica)
  8. additionThe fractions containing pure product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0ba62e079e6e49fe81a31d835f78ee45
Source dataset
uspto-grants-1995_05
Patent number
US05419966

Linked notes

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