Ethyl Acetate → 2,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

HRID 857813Notes

Reaction equation

HRID 857813 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][C:7]2=[C:9](C(O)=O)[S:10][C:11](C(O)=O)=[C:6]2[O:5][CH2:4]1.C(OCC)(=O)C>CN(C)C(=O)C.N1C2C(=CC=CC=2)C=CC=1>[O:8]1[CH:3]([CH2:2][OH:1])[CH2:4][O:5][C:6]2=[CH:11][S:10][CH:9]=[C:7]12

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 219583572-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

Product 1

HCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

Reagents, catalysts & solvents 2

HCID 7047QuinolineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid (48 g, 0.184 mol) was dissolved in N,N-dimethylacetamide (500 mL), and Cu2Cr2O7 (8.6 g) and quinoline (15 drops) were added. This mixture was subsequently stirred for 2 hours at 150° C., after which it was cooled to 25° C. It was then poured into ethyl acetate, the catalyst was removed by filtration and the filtrate was washed with acidic water and aqueous, saturated NaCl. Subsequently, the solvent was removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol was isolated by vacuum distillation (115–120° C.; 0.05 mm Hg).

Workup

  1. temperatureafter which it was cooled to 25° C
  2. customthe catalyst was removed by filtration
  3. washthe filtrate was washed with acidic water
  4. customSubsequently, the solvent was removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol
  5. customwas isolated by vacuum distillation (115–120° C.; 0.05 mm Hg)

Sources & evidence

ORD record
ord-0af733afca284fdb953951fc7d88fe0d
Source dataset
uspto-grants-2006_12
Patent number
US07147936B2

Reaction notes

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