Ethanol → 6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-propanoic acid

HRID 370588Notes

Reaction equation

HRID 370588 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.S1(CCCC1)(=O)=O.[C:22]([C:25]1[CH:43]=[CH:42][CH:41]=[CH:40][C:26]=1[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:39])C(O)=O)=[CH:31][CH:30]=1)([OH:24])=O.[OH-:44].[Na+].[CH2:46]([OH:48])C>>[O:24]=[C:22]1[C:25]2[CH:43]=[CH:42][CH:41]=[CH:40][C:26]=2[CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([CH2:35][CH2:39][C:46]([OH:48])=[O:44])=[CH:33][C:34]1=2

Participants

6

Reactant 5

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 31347SulfolaneHCID 122923134-(2-Carboxybenzyloxy)phenylpropanoic acid

Product 1

HCID 123929606,11-Dihydro-11-oxodibenz[b,e]oxepin-2-propanoic acidYield 68%

Conditions

Temperature
110 °C

Procedure

Phosphorus pentoxide (10.4 g, 0.073 mole) was cautiously added to 7.4 ml of absolute ethanol under a nitrogen atmosphere and stirred at 110° C. for 1 hour; 53.1 ml of sulfolane was added and the temperature adjusted to 85° C. After adding 4-(2-carboxybenzyloxy)phenylpropanoic acid of Example 6a (5.0 g, 0.017 mole), the reaction was stirred at 85° C. for 3.5 hours. The mixture was poured into 1 liter of ice water, made basic by addition of NaOH pellets, extracted with toluene and the aqueous phase was then acidified with concentrated HCl. The resulting precipitate was filtered, triturated with isopropanol and dried giving 3.22 g of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-propanoic acid (68% yield), m.p. 128°-130° C.

Workup

  1. customadjusted to 85° C
  2. stirringthe reaction was stirred at 85° C. for 3.5 hours
  3. extractionextracted with toluene
  4. filtrationThe resulting precipitate was filtered
  5. customtriturated with isopropanol
  6. customdried

Sources & evidence

ORD record
ord-5d75c41806c341b7b3a16951a93b0823
Source dataset
uspto-grants-1985_07
Patent number
US04526891

Reaction notes

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