Carbon Dioxide → 2,4,6-Tris(1-methylethyl)benzoic acid

HRID 529863Notes

Reaction equation

HRID 529863 reaction equation
Br[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([CH:11]([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH:14]([CH3:16])[CH3:15].[C:17](=[O:19])=[O:18].Cl>>[CH:14]([C:3]1[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH:6]=[C:7]([CH:8]([CH3:10])[CH3:9])[C:2]=1[C:17]([OH:19])=[O:18])([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 280Carbon Dioxide2×HCID 313Hydrochloric AcidHCID 1408461-Bromo-2,4,6-triisopropylbenzene

Product 1

HCID 962142,4,6-Tris(1-methylethyl)benzoic acidYield 80%

Procedure

A Grignard reagent was prepared from 56.7 g of 1-bromo-2,4,6-triisopropylbenzene and poured to 300 g of dry ice, whereupon dry ice sublimated. Hydrochloric acid was added to the reaction mixture for quenching, followed by extraction with 200 g of toluene. The organic layer was taken out, washed with water, and combined with 10 wt % sodium hydroxide aqueous solution. The aqueous layer was taken out, combined with 50 g of 35 wt % hydrochloric acid, and extracted with 200 g of toluene. The organic layer was washed with water again, and concentrated under reduced pressure. The concentrate was crystallized from 150 g of hexane. The crystal precipitate was filtered and dried, obtaining the target compound, 2,4,6-triisopropylbenzoic acid. Amount 39.7 g, yield 80%.

Workup

  1. customfor quenching
  2. extractionfollowed by extraction with 200 g of toluene
  3. washwashed with water
  4. extractionextracted with 200 g of toluene
  5. washThe organic layer was washed with water again
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate was crystallized from 150 g of hexane
  8. filtrationThe crystal precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-67b5961fae7243d6bd5a2ff3e126bb2b
Source dataset
uspto-grants-2016_05
Patent number
US09348227B2

Reaction notes

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