Carbon Dioxide → 2,4,6-Tricyclohexylbenzoic acid

HRID 529867Notes

Reaction equation

HRID 529867 reaction equation
Br[C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][C:5]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:4][C:3]=1[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[C:26](=[O:28])=[O:27].Cl>>[CH:20]1([C:3]2[CH:4]=[C:5]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:6]=[C:7]([CH:8]3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]3)[C:2]=2[C:26]([OH:28])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 280Carbon Dioxide2×HCID 313Hydrochloric AcidHCID 670505411,3,5-Tricyclohexylbromobenzene

Product 1

HCID 898320272,4,6-Tricyclohexylbenzoic acidYield 80%

Procedure

A Grignard reagent was prepared from 28.4 g of 2-bromo-1,3,5-tricyclohexylbenzene (prepared in Synthesis Example 1-4) 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 isopropyl ether. The organic layer was taken out, washed with water, and combined with 150 g of 10 wt % sodium hydroxide aqueous solution. The aqueous layer was taken out, combined with 100 g of 35 wt % hydrochloric acid, and extracted with 200 g of diisopropyl ether. 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-tricyclohexylbenzoic acid. Amount 39.7 g, yield 80%.

Workup

  1. customfor quenching
  2. extractionfollowed by extraction with 200 g of isopropyl ether
  3. washwashed with water
  4. extractionextracted with 200 g of diisopropyl ether
  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-670a80d6f6d74395956a53fe0e7991a1
Source dataset
uspto-grants-2016_05
Patent number
US09348227B2

Reaction notes

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