Phosphorus oxide (P4O10) → HCID 22152299, compound

HRID 1111333Notes

Reaction equation

HRID 1111333 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.CCCCCC>[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

5

Reactant 2

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

Product 1

HCID 22152299HCID 22152299, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidSolventHCID 8058HexaneSolvent

Procedure

To a solution of 50 g (0.352 mol) of phosphorous pentoxide in 500 ml of methanesulfonic acid was added dropwise 20 g (0.101 mol) of 1-(3-methoxyphenoxy)-2-methyl-2-propanol over a 30 min period. The reaction mixture was stirred for 3 h at ambient temperature. The reaction mixture was poured into 1.5 l of ice water and extracted with ether. The combined extracts were dried and evaporated. The residue was filtered through silica gel (500 g) using a gradient from hexane to 10:90 (v/v) of ether:hexane as eluent, There was obtained 13.2 g (74.06 mmol, 72%) of 2,3-dihydro-6-methoxy-3,3-dimethylbenzofuran. This material was dissolved in 75 ml of toluene an 8.12 g (0.11 mol) of dimethylformamide was added. The mixture was cooled in an ice water bath and 14.23 g (92.8 mmol) of phosphorous oxytrichloride was added dropwise. The reaction mixture was heated at reflux for 3 h. The reaction mixture was cooled to ambient temperature and poured into 300 ml of 2N sodium hydroxide solution. The organic phase was washed with 1N hydrochloric acid, water, saturated sodium chloride solution, dried and evaporated. The residue was chromatographed on silica gel (150 g) using a gradient of from hexane to 25:75 (v/v) ether:hexane as eluent. There was obtained 10.3 g (49.9 mmol, 68%) of 2,3-dihydro-6-methoxy-3,3-dimethyl-5-benzofurancarboxaldehyde as white crystals; mp 75°-76° C.

Workup

  1. extractionextracted with ether
  2. customThe combined extracts were dried
  3. customevaporated
  4. filtrationThe residue was filtered through silica gel (500 g)

Sources & evidence

ORD record
ord-4bcffd5144de4501be4b689902e99479
Source dataset
uspto-grants-1990_12
Patent number
US04980352

Reaction notes

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