Carbon Dioxide → HCID 14315188, compound

HRID 467336Notes

Reaction equation

HRID 467336 reaction equation
[CH2:1]([S:11][C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Mg].II.[C:22](=[O:24])=[O:23].Cl>O1CCCC1.O>[CH2:1]([S:11][C:12]1[CH:17]=[CH:16][C:15]([C:22]([OH:24])=[O:23])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 807IodineHCID 5462224MagnesiumHCID 19813937HCID 19813937, compound

Product 1

HCID 14315188HCID 14315188, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of 4-(decylthio)bromobenzene (32.9 g) in dry tetrahydrofuran (100 ml) was added over about 30 minutes to a stirred, refluxing suspension of magnesium turnings (2.64 g) and one crystal of iodine in dry tetrahydrofuran (100 ml). The mixture was then stirred at reflux for 2 hours after which it was cooled to -70° C. Carbon dioxide was passed through the stirred solution at -70° C. for about 2 hours. The solution was warmed to room temperature and was then poured into a mixture of ice and water (1.251). Hydrochloric acid was added to bring the pH to 1, the precipitate was collected and washed with water, dried and then crystallized from cyclohexane to yield 4-(decylthio)benzoic acid (20.29 g) in the form of white crystals, m.p. 108°-109° C. [Elemental analysis: C,69.2; H,8.9; S,11.1%; calculated: C,69.34; H,8.9; S,10.88%].

Workup

  1. temperaturerefluxing
  2. temperatureat reflux for 2 hours after which it
  3. temperatureThe solution was warmed to room temperature
  4. customthe precipitate was collected
  5. washwashed with water
  6. customdried
  7. customcrystallized from cyclohexane

Sources & evidence

ORD record
ord-17b0272fcf8241af83227d485ccd5bb9
Source dataset
uspto-grants-1992_10
Patent number
US05159114

Reaction notes

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