Phenylacetic Acid → 1-(4-Methoxyphenyl)-2-phenylethan-1-one

HRID 1728356Notes

Reaction equation

HRID 1728356 reaction equation
CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:20]1([CH2:26][C:27]([OH:29])=O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:30]1([O:36][CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)(O)[O-].[Na+]>>[CH3:37][O:36][C:30]1[CH:35]=[CH:34][C:33]([C:27](=[O:29])[CH2:26][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 5

HCID 999Phenylacetic AcidHCID 6395Methanesulfonic AcidHCID 7519AnisoleHCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium Bicarbonate

Product 1

HCID 2310931-(4-Methoxyphenyl)-2-phenylethan-1-oneYield 87.8%

Procedure

A mixture of methanesulfonic acid (100 g) and P2O5 (10 g) was stirred at 50°-60° C. until solution was complete, then cooled to room temperature. To this was added phenylacetic acid (2.0 g) and anisole (4.00 g). The mixture was stirred at 50°-60° C. for 90 minutes, cooled to room temperature and poured into ice water (1.2 L). The solution was made basic by gradual addition of solid sodium bicarbonate, then extracted into ethyl acetate (800 mL). The ethyl acetate was dried over magnesium sulfate and evaporated to give 3.88 grams of crude product. This crude product was chromatographed on silica gel eluting with 2% ethyl acetate in hexane, to obtain 2.92 grams of 1-(4-methoxyphenyl)-2-phenylethanone.

Workup

  1. stirringThe mixture was stirred at 50°-60° C. for 90 minutes
  2. temperaturecooled to room temperature
  3. extractionextracted into ethyl acetate (800 mL)
  4. dry with materialThe ethyl acetate was dried over magnesium sulfate
  5. customevaporated
  6. customto give 3.88 grams of crude product
  7. customThis crude product was chromatographed on silica gel eluting with 2% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d27030f1cd8840bcb513c472046692f9
Source dataset
uspto-grants-1994_07
Patent number
US05326762

Reaction notes

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