Carbon Dioxide → HCID 15708385, compound

HRID 1073067Notes

Reaction equation

HRID 1073067 reaction equation
[C:1](=[O:3])=[O:2].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[CH:17]=[CH:16][C:15]=2Br)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[Mg].Cl.[OH-].[Na+]>O1CCCC1.O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[CH:17]=[CH:16][C:15]=2[C:1]([OH:3])=[O:2])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

8

Reactant 5

HCID 280Carbon Dioxide2×HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5462224MagnesiumHCID 15708388HCID 15708388, compound

Product 1

HCID 15708385HCID 15708385, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dry carbon dioxide from -5° to 0° is introduced into a solution consisting of 20,0 g of 1-(3,4-dimethoxyphenyl)-6-chloro-2-bromomagnesium naphthalene in 110 ml of tetrahydrofurane, made from 18,8 g of 1-(3,4-dimethoxyphenyl)-6-chloro-2-bromonaphthalene and 1,2 of magnesium. The introduction of carbon dioxide is continued for one hour after the exothermic reaction is finished. While cooling, 30 ml of 10% hydrochloric acid and thereafter 200 ml of water are then added dropwise, and the acid reaction solution is rendered alkaline with concentrated sodium hydroxide solution and extracted twice with 150 ml of ether each time. The aqueous phase is adjusted to pH 1 with 20% hydrochloric acid. The acid which precipitates is filtered off, washed with a small amount of water and dried in a vacuum drying cabinet at 80°. M.p. of the beige title compound >200°.

Workup

  1. customafter the exothermic reaction
  2. temperatureWhile cooling
  3. customthe acid reaction solution
  4. extractionextracted twice with 150 ml of ether each time
  5. customThe acid which precipitates
  6. filtrationis filtered off
  7. washwashed with a small amount of water
  8. customdried in a vacuum
  9. customdrying cabinet at 80°
  10. customM.p. of the beige title compound >200°

Sources & evidence

ORD record
ord-29142a7619944190824c3480ca45dbee
Source dataset
uspto-grants-1990_11
Patent number
US04968677

Reaction notes

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