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Dimethylformamide → Methyl 4-Benzoyl-3-hydroxyphenoxyacetate

HRID 1493414
Notes
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Reaction equation

HRID 1493414 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(O)C>[C:4]([C:3]1[CH:12]=[CH:13][C:14]([O:16][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][C:2]=1[OH:1])(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 85722,4-DihydroxybenzophenoneHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 14618907Methyl 4-Benzoyl-3-hydroxyphenoxyacetateYield 69%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Conditions

Temperature
25 °C

Procedure

A mixture of 15.0 g (70.0 mmol) of 2,4-dihydroxybenzophenone, 10.7 g (70 mmol) of methyl bromoacetate, 19.3 g (0.14 mol) of potassium carbonate, and 125 ml of N,N-dimethylformamide is stirred at 25° C. for 18 hours. The reaction mixture is partitioned between diethyl ether and 0.5 N hydrochloric acid. Solids are removed by filtration, and the filtrate is dried over magnesium sulfate and concentrated. The concentrate is partially dissolved in diethyl ether, and solids are removed by filtration. The solid material is recrystallized from dichloromethane: 2-propanol to afford 13.7 g (69% yield) of the title compound, a pale yellow solid, mp 131°-4° C.

Workup

  1. customThe reaction mixture is partitioned between diethyl ether and 0.5 N hydrochloric acid
  2. customSolids are removed by filtration
  3. dry with materialthe filtrate is dried over magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe concentrate is partially dissolved in diethyl ether
  6. customsolids are removed by filtration
  7. customThe solid material is recrystallized from dichloromethane

Sources & evidence

ORD record
ord-7c11d4a2427e41058ea5fcbcb5819b06
Source dataset
uspto-grants-1991_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05021478

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes