Methanol → HCID 54457050, compound

HRID 866786Notes

Reaction equation

HRID 866786 reaction equation
[OH-].[Na+].CO.[CH3:5][C:6]1([CH3:26])[C@@H:8]([C:9]([O-:11])=[O:10])[C@@H:7]1[CH:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[CH3:5][C:6]1([CH3:26])[C@@H:8]([C:9]([OH:11])=[O:10])[C@@H:7]1[CH:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86734266HCID 86734266, compound

Product 1

HCID 54457050HCID 54457050, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

42.7 cc of a 2N methanolic sodium hydroxide solution were introduced into 100 cc of methanol and 10 cc of water, followed by 18.45 gm of ethyl dl-trans 3,3-dimethyl-2-(2',2'-diphenylvinyl)-cyclopropanecarboxylate were added thereto. The mixture was brought to reflux and maintained there for 1 hour and 30 minutes. The methanol was removed by distillation and water was added. Next the aqueous phase was extracted with ethyl ether to eliminate the neutral fraction and the combined ether extracts were washed with water and the wash water was combined with the principal aqueous phase. Then the entire aqueous phase was acidified with a dilute aqueous solution of hydrochloric acid which was then repeatedly extracted with methylene chloride; the methylene chloride solutions were combined, washed with water, dried and concentrated to dryness to obtain 7.95 gm of dl-trans 3,3-dimethyl-2-(2',2'-diphenylvinyl)-cyclopropanecarboxylic acid having a melting point of 115° C. A sample of this product crystallized from a mixture of isopropyl ether and petroleum ether, had a melting point of 115° C.

Workup

  1. additionwere added
  2. temperatureto reflux
  3. temperaturemaintained there for 1 hour and 30 minutes
  4. customThe methanol was removed by distillation and water
  5. additionwas added
  6. extractionNext the aqueous phase was extracted with ethyl ether
  7. washthe combined ether extracts were washed with water
  8. extractionwas then repeatedly extracted with methylene chloride
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7030bd7f023c4a3d89c4c3a9b112dc99
Source dataset
uspto-grants-1978_07
Patent number
US04101574

Reaction notes

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