Acetone → HCID 58070862, compound

HRID 1193029Notes

Reaction equation

HRID 1193029 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:20]=[CH:19][O:18][C:17]=2[CH2:21]O)=[C:11]([CH3:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:26]>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:23])[C:12]([CH:16]2[C:20](=[O:26])[CH:19]=[CH:21][CH:17]2[OH:18])=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 180Acetone2×HCID 66709635HCID 66709635, compound

Product 1

HCID 58070862HCID 58070862, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Polyphosphoric acid (5 g) is added to a warm (55° C.) solution of ([4-benzyloxy-2,6-dimethylphenyl]furan-2-yl)methanol (32 g) in a mixture of acetone (400 ml) and water (100 ml) and the mixture is heated at 55° C. for 20 hours. The reaction mixture is cooled to room temperature and most of the acetone is removed under reduced pressure. The mixture is extracted with diethyl ether (3×250 ml), and the organic fractions are washed with saturated aqueous sodium bicarbonate solution (2×200 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The crude product (30.9 g) is used for the next step without further purification.

Workup

  1. customis removed under reduced pressure
  2. extractionThe mixture is extracted with diethyl ether (3×250 ml)
  3. washthe organic fractions are washed with saturated aqueous sodium bicarbonate solution (2×200 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe crude product (30.9 g) is used for the next step without further purification

Sources & evidence

ORD record
ord-652ed1cfd7c548c4a577d4a4ecd5ca66
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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