Water → Phenacyl 4-hydroxymethylphenoxyacetate

HRID 865444Notes

Reaction equation

HRID 865444 reaction equation
[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].C(N(CC)CC)C.O>CN(C=O)C>[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([O:11][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 1942914-Hydroxymethylphenoxyacetic acid

Product 1

HCID 11954711Phenacyl 4-hydroxymethylphenoxyacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

182 g of 4-hydroxymethylphenoxyacetic acid and 199 g of α-bromoacetophenone are dissolved in 600 ml of dry DMF, and then, at 0° C., 138 ml of triethylamine are rapidly added dropwise. The mixture is allowed to reach room temperature, and is stirred overnight. The DMF solution is poured into 3.5 1 of water, and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and concentrated. The product precipitates out on evaporation. It is filtered off with suction, washed with ethyl acetate/n-hexane 1:1 and dried under high vacuum.

Workup

  1. customto reach room temperature
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product precipitates out on evaporation
  7. filtrationIt is filtered off with suction
  8. washwashed with ethyl acetate/n-hexane 1:1
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-1d4d0bea01b145a0afbc224b7d555354
Source dataset
uspto-grants-1996_10
Patent number
US05565606

Reaction notes

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