Toluene → 5-methyl-2-phenyl-1,3,2-dioxaborinane-5-carboxylic Acid

HRID 860704Notes

Reaction equation

HRID 860704 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5].[C:10]1([B:16](O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC=CC=1>O1CCCC1>[CH3:7][C:3]1([C:4]([OH:6])=[O:5])[CH2:8][O:9][B:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:1][CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 78501Dimethylolpropionic acid

Product 1

HCID 113790015-methyl-2-phenyl-1,3,2-dioxaborinane-5-carboxylic AcidYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2,2-bis(hydroxymethyl)propionic acid (131 g, 0.98 mole) in tetrahydrofuran (500 ml) was added a solution of phenylboronic acid (122 g, 1.0 mole) in tetrahydrofuran (500 ml). The mixture was stirred for 3 h and toluene (1.0 L) was added. Water was removed by azeotropic distillation with toluene. Heptanes (500 ml) was added to the precipitated product, heated to reflux and cooled. The mixture was filtered and washed with heptanes (2×300 ml). The solids were dried under vacuum at 70–75° C. until constant weight to give 94% yield. 1H NMR: δ (DMSO-d6) 7.65 (d, 2H, Ar), 7.40 (m, 3H, Ar), 4.35 (d, 2H, CH2), 3.92 (d, 2H, CH2), 1.17 (s, 3H, CH3)

Workup

  1. customWater was removed by azeotropic distillation with toluene
  2. additionHeptanes (500 ml) was added to the precipitated product
  3. temperatureheated
  4. temperatureto reflux
  5. temperaturecooled
  6. filtrationThe mixture was filtered
  7. washwashed with heptanes (2×300 ml)
  8. customThe solids were dried under vacuum at 70–75° C. until constant weight
  9. customto give 94% yield

Sources & evidence

ORD record
ord-5c4eedbadcfa491786c6d6faf1bb2436
Source dataset
uspto-grants-2006_12
Patent number
US07153957B2

Reaction notes

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