2-Phenylacetophenone → HCID 13298045, compound

HRID 982420Notes

Reaction equation

HRID 982420 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:22][CH:23]1[CH2:28]CCCO1.[OH-].[Na+]>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-].O>[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:22][CH2:23][CH2:28][CH:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:8]

Participants

6

Reactant 3

HCID 99482-PhenylacetophenoneHCID 14798Sodium HydroxideHCID 263182Tetrahydropyranyl ether

Product 1

HCID 13298045HCID 13298045, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture containing 19.6 g of desoxybenzoin, 20.9 g of tetrahydropyran-2-yl ether-protected bromoethanol, 1.0 g of TEBAC and 50 ml of 48% sodium hydroxide solution is stirred for 2 h at 75° C. Water is added and the product extracted in toluene. The toluene solution is washed with water and dried over sodium sulfate. Finally the solvent is evaporated. The yield is quantitative, but the oily product contains about 20% O-alkylation product.

Workup

  1. extractionthe product extracted in toluene
  2. washThe toluene solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. customFinally the solvent is evaporated

Sources & evidence

ORD record
ord-58586386a45444c18efa56268b909cbc
Source dataset
uspto-grants-1991_02
Patent number
US04996225

Reaction notes

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