Phosphorus oxide (P4O10) → HCID 22152299, compound

HRID 1496996Notes

Reaction equation

HRID 1496996 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:26]=[CH:27][CH:28]=1)[O:20][CH2:21][C:22]([CH3:25])(O)[CH3:23]>CS(O)(=O)=O>[CH3:15][O:16][C:17]1[CH:28]=[CH:27][C:26]2[C:22]([CH3:25])([CH3:23])[CH2:21][O:20][C:19]=2[CH:18]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 22152286HCID 22152286, compound

Product 1

HCID 22152299HCID 22152299, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

To a solution of phosphorous pentoxide (55.1 g, 383 mmol) in methanesulfonic acid (100 mL) was added drop wise 1-(3-methoxyphenoxy)-2-methylpropan-2-ol (25 g, 127.6 mmol) over a 30 min period. The reaction mixture was stirred for 3 h at r.t. The reaction mixture was poured into 500 mL of ice water and extracted with ether (200 mL×3). The combined extracts were dried and evaporated. The residue was purified by silica gel column chromatography eluting with petroleum ether/ether (9:1) to afford 6-methoxy-3,3-dimethyl-2,3-dihydrobenzofuran (5.5 g, 25%) as a yellow oil.

Workup

  1. extractionextracted with ether (200 mL×3)
  2. customThe combined extracts were dried
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with petroleum ether/ether (9:1)

Sources & evidence

ORD record
ord-645d721c2fa741e0ae3cfea4d6fe16c2
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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