Carbon Dioxide → HCID 23714060, compound

HRID 1701079Notes

Reaction equation

HRID 1701079 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]=1[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(C1C=CC=C(OC2C=CC=CC=2)C=1)C1C=CC=CC=1.C[Li].C([Li:50])CCC.O(C1C=CC=C(OC2C=CC=CC=2)C=1[Li])C1C=CC=CC=1.C(=O)=O>CCOCC.O1CCCC1>[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:9]=1[C:10]([O-:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[Li+:50]

Participants

9

Reactant 6

HCID 280Carbon Dioxide2×HCID 76911Benzene, 1,3-diphenoxy-HCID 15872348HCID 15872348, compoundHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compoundHCID 178506763HCID 178506763, compound

Product 1

HCID 23714060HCID 23714060, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

The desired 2,6-diphenoxybenzoic acid can be prepared as illustrated in equation 1 ##STR4## In this method, 1,3-diphenoxybenzene is caused to react with an alkyllithium compound ZLi where Z is alkyl of 1 to 4 carbon atoms or phenyl, for example, methyllithium or butyllithium, in an ether-type solvent such as diethyl ether or tetrahydrofuran for 0.5 to 3 hours at 25°-100°, preferably at the boiling point of the solvent. The resulting intermediate, 2,6-diphenoxyphenyllithium, is added to an excess of solid carbon dioxide, or a mixture of solid carbon dioxide in ether, and the mixture is allowed to warm to room temperature to yield lithium 2,6-diphenoxybenzoate. Addition of a mineral acid, HX, such as hydrochloric acid or sulfuric acid, yields 2,6-diphenoxybenzoic acid.

Sources & evidence

ORD record
ord-4a365c3846f04779b4f7e85a0258598e
Source dataset
uspto-grants-1980_03
Patent number
US04191554

Reaction notes

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