Toluene → 2-[1,1′-Biphenyl]-4-yl-1,3-dioxane-5,5-dimethanol

HRID 537340Notes

Reaction equation

HRID 537340 reaction equation
[CH3:1][C:2](N(C)C)=[O:3].C1(C)C=CC=CC=1.[OH:14][CH2:15][C:16]([CH2:21][OH:22])([CH2:19][OH:20])[CH2:17]O.[C:23]1([C:31]2[CH:36]=[CH:35]C=[CH:33][CH:32]=2)[C:24](C=O)=[CH:25][CH:26]=[CH:27][CH:28]=1>O>[C:31]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:32]=[CH:33][C:1]([CH:2]2[O:3][CH2:17][C:16]([CH2:21][OH:22])([CH2:19][OH:20])[CH2:15][O:14]2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8285PentaerythritolHCID 31374DimethylacetamideHCID 121052(1,1'-Biphenyl)-2-carboxaldehyde

Product 1

HCID 468420482-[1,1′-Biphenyl]-4-yl-1,3-dioxane-5,5-dimethanolYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 5,000 ml flask was charged with 2,000 ml of DMAc, 1,400 ml of toluene, 200 g (1.47 mol) of pentaerythritol, 134 g (0.74 mol) of biphenylaldehyde and 20 g of paratoluenesulfonic acid dihydrate, and the mixture was stirred at 100° C. Then, it heated up to 145° C. A distillate containing water was separated, and the reaction was finished in a reaction time of 5 hours. 5 L of water was put into the reaction liquid, and white crystals were deposited. They were filtrated, washed with water and then concentrated to thereby obtain white crystals (yield: 90%). It was identified from chemical shift values of 1H-NMR that the compound obtained in the present example was the same compound as the compound obtained in Example 1.

Workup

  1. temperatureThen, it heated up to 145° C
  2. customwas separated
  3. customwas finished in a reaction time of 5 hours
  4. custom5 L of water was put into the reaction liquid, and white crystals
  5. filtrationThey were filtrated
  6. washwashed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c967cd544e2044b0b8182dd84b89b393
Source dataset
uspto-grants-2014_10
Patent number
US08859787B2

Reaction notes

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