(+-)-4-Hydroxymandelic acid → HCID 15280379, compound

HRID 2092498Notes

Reaction equation

HRID 2092498 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.CO[C:15](OC)([CH3:17])[CH3:16].B(F)(F)F.CCOCC.C(N(CC)CC)C>CC(C)=O>[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]2[O:10][C:15]([CH3:17])([CH3:16])[O:8][C:7]2=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 328(+-)-4-Hydroxymandelic acidHCID 64952,2-DimethoxypropaneHCID 8000Boron trifluoride etherateHCID 8471Triethylamine

Product 1

HCID 15280379HCID 15280379, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of commercial 4-hydroxy-mandelic acid (10.0 gr, 0.05 mol) in acetone (160 ml), 2,2-dimethoxypropane (56 mL, 0.45 mol) and BF3.Et2O (0.4 ml, 0.48 mol)) were added under vigorous stirring. The solution was left stirring for 3 hours. After adding of triethylamine (TEA) (2 mL), the solvent was evaporated under vacuum and the crude diluted in a saturated solution of Na2HCO3 (30 ml) and extracted with EtOAc (3×30 ml). The collected organic extracts were washed with brine (2×25 mL), dried over Na2SO4 and evaporated under vacuum to give the intermediate 5-(4-hydroxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-one (10.21 g) as yellow oil, pure enough to be used in the further step without any purification.

Workup

  1. waitThe solution was left
  2. customthe solvent was evaporated under vacuum
  3. additionthe crude diluted in a saturated solution of Na2HCO3 (30 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. washThe collected organic extracts were washed with brine (2×25 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-b3275230af4648e6998915cfe0c6a4ec
Source dataset
uspto-grants-2013_05
Patent number
US08440711B2

Reaction notes

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