Carbon Dioxide → HCID 15872348, compound

HRID 1701080Notes

Reaction equation

HRID 1701080 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.C[Li].[C:28](=[O:30])=[O:29]>C(OCC)C.O>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]=1[C:28]([OH:30])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 76911Benzene, 1,3-diphenoxy-HCID 178418348HCID 178418348, compound

Product 1

HCID 15872348HCID 15872348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 11 parts of 1,3-diphenoxybenzene and 40 parts of tetrahydrofuran is added 1 part of methyllithium (as a 1.82 M solution in diethyl ether) while the mixture is cooled in an ice bath. The resulting solution is heated under reflux for 2 hours and then is poured slowly onto 500 parts of dry ice. After the mixture has warmed to room temperature, 100 parts of water are added, and the tetrahydrofuran is evaporated. After the aqueous solution is extracted with 50 parts diethyl ether, it is then acidified with concentrated hydrochloric acid. The white solid which forms is collected to yield 12 parts of 2,6-diphenoxybenzoic acid. The compound is purified by recrystallization from acetonitrile to give 8 parts of pure material, M.P. 164°-165°.

Workup

  1. temperatureis cooled in an ice bath
  2. temperatureThe resulting solution is heated
  3. temperatureunder reflux for 2 hours
  4. customthe tetrahydrofuran is evaporated
  5. extractionAfter the aqueous solution is extracted with 50 parts diethyl ether, it
  6. customThe white solid which forms is collected

Sources & evidence

ORD record
ord-03c9d72518e6471592b8725e3bec40a8
Source dataset
uspto-grants-1980_03
Patent number
US04191554

Reaction notes

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