Hydrochloric Acid → 1-Chloro-3-phenoxypropan-2-one

HRID 613977Notes

Reaction equation

HRID 613977 reaction equation
[N+](=[CH2:3])=[N-].[O:4]([CH2:11][C:12](Cl)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[ClH:15]>C(OCC)C>[Cl:15][CH2:3][C:12]([CH2:11][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 69703Phenoxyacetyl chloride

Product 1

HCID 116224561-Chloro-3-phenoxypropan-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of diazomethane (ca 6 g = 0.141 mmol) in ethyl ether (400 ml) was added over 2 hours at 1°-3° phenoxyacetyl chloride (11.95 g = 0.07 mole) dissolved in ethyl ether (50 ml). The mixture was stirred at the same temperature for 2 more hours and was allowed to stand overnight at room temperature. Then 5.5 N hydrochloric acid (25 ml, 0.137 moles) was added with stirring over 110 min. at 16°-20°. After the mixture was stirred for an additional 4 hours, the layers were separated and the ether layer was washed with three 80 ml portions of water and dried over anhydrous sodium sulfate. Removal of the solvent gave the crude product as a yellow oil, 13 g (100%); ir (film, cm-1) 1740, 1595, 1495, 1240; nmr (DCCl3, ppm) 7.40-6.70 (m, 5H), 4.60 (s, 2H), 4.25 (s, 2H). This product was used without purification to prepare phenoxyacetylmethyltriphenylphosphonium chloride.

Workup

  1. stirringwith stirring over 110 min. at 16°-20°
  2. stirringAfter the mixture was stirred for an additional 4 hours
  3. customthe layers were separated
  4. washthe ether layer was washed with three 80 ml portions of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-4072ea5ca7154ba4aa9feb2e9688eadf
Source dataset
uspto-grants-1979_03
Patent number
US04143046

Reaction notes

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