Sodium Hydroxide → Isoxepac

HRID 1195023Notes

Reaction equation

HRID 1195023 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C1S(=O)(=O)CCC1.[C:22]([C:25]1[CH:42]=[CH:41][CH:40]=[CH:39][C:26]=1[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]([OH:38])=[O:37])=[CH:31][CH:30]=1)([OH:24])=O.[OH-].[Na+]>C(O)C>[O:24]=[C:22]1[C:25]2[CH:42]=[CH:41][CH:40]=[CH:39][C:26]=2[CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][C:36]([OH:38])=[O:37])=[CH:31][C:30]1=2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 31347SulfolaneHCID 122923092-((4-Carboxymethylphenoxy)methyl)benzoic acid

Product 1

HCID 41448Isoxepac

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 49 ml. of absolute ethanol is added with vigorous stirring, 81 g. of phosphorus pentoxide. After addition, the mixture is allowed to stir at 95°-100° C. for 1 hour, 400 ml. of tetramethylene sulfone are added, and the temperature is adjusted to 86°-90° C. Then, 38.5 g. of 4-(2-carboxybenzyloxy)phenylacetic acid are added, the mixture is stirred for 4 hours and poured onto ice water. The aqueous mixture is made basic with sodium hydroxide and extracted with toluene. Cooling of the aqueous layer followed by acidification with concentrated hydrochloric acid gives light brown crystals. Recrystallization from acetic acid-water or from dimethoxyethane provides colorless crystals, m.p. 126°-128° C. of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid.

Workup

  1. additionAfter addition
  2. customis adjusted to 86°-90° C
  3. stirringthe mixture is stirred for 4 hours
  4. additionpoured onto ice water
  5. extractionextracted with toluene
  6. temperatureCooling of the aqueous layer
  7. customgives light brown crystals
  8. customRecrystallization from acetic acid-water

Sources & evidence

ORD record
ord-9b4a6ab81cdd4f9295f12050600f5cd5
Source dataset
uspto-grants-1989_03
Patent number
US04816591

Reaction notes

Loading…