Acetic Acid → methyl 3-oxo-3,4-dihydro-2H-1,5-benzodioxepin-2-carboxylate

HRID 267787Notes

Reaction equation

HRID 267787 reaction equation
[K].[O-]CCCC.[C:7]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])(OC)=[O:8].C(O)(=O)C>CS(C)=O.O>[O:8]=[C:7]1[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH:20]1[C:21]([O:23][CH3:24])=[O:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 347859Methyl 2-methoxycarbonylmethyloxyphenoxyacetateHCID 5462222PotassiumHCID 12476378Butan-1-olate

Product 1

HCID 13544514methyl 3-oxo-3,4-dihydro-2H-1,5-benzodioxepin-2-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Potassium t.-butoxide (15.8 g.) dissolved in DMSO (130 ml.) is added dropwise over a 45 minute period to 1,2-bis-carbomethoxymethoxybenzene (18.3 g.) in DMSO (30 ml.) under an atmosphere of nitrogen. The mixture then is stirred 3 hours at ambient temperature and a mixture of acetic acid (16 ml.) and water (200 ml.) is added. The reaction mixture is extracted with benzene, the powdery material removed by filtration and the benzene then dried over magnesium sulfate and the benzene then evaporated leaving 3-oxo-4-carbomethoxy-3,4-dihydro-2H-1,5-benzodioxepin that is used in the following step without purification.

Workup

  1. additionis added
  2. extractionThe reaction mixture is extracted with benzene
  3. customthe powdery material removed by filtration
  4. dry with materialthe benzene then dried over magnesium sulfate
  5. customthe benzene then evaporated

Sources & evidence

ORD record
ord-766110ea60d7478594a1f48108ef4b28
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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