Carbon Dioxide → HCID 23683138, compound

HRID 2390598Notes

Reaction equation

HRID 2390598 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=[O:5].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26].[Na].[OH-].[Na+:32].C(=O)=O>C(O)(C)C.CC(OC)(C)C.O>[OH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O-:27])=[O:26])=[O:5].[Na+:32]

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 14798Sodium Hydroxide2×HCID 700382,2'-DihydroxybenzophenoneHCID 264813Ethyl 8-bromooctanoateHCID 5360545Sodium

Product 1

HCID 23683138HCID 23683138, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

Starting from 2,2′-dihydroxybenzophenone and ethyl 8-bromooctanoate, the title compound was prepared and then converted into the sodium salt as follows: the free acid (3.56 g, 9.99 mmol) was dissolved in 40 mL of isopropanol, and treated with sodium hydroxide solution (1.7 mL) prepared from of sodium hydroxide (0.90 g, 22.5 mmol) and water (3.7 mL). Isopropanol and MTBE were added causing a solid to precipitate. Heating this mixture caused most of the solid to dissolve. The remaining solids were removed by filtration. The off-white solid that formed upon cooling with dry ice was isolated by filtration and dried under reduced pressure. Combustion analysis: Found: C, 65.02%; H, 6.22%; C21H23O5Na requires C, 66.00; H, 6.65%; 1H NMR (d6-DMSO): δ 12.6, bs, 1H (OH); δ 7.41, t, 1H, (aryl H); δ 7.31, t, 1H (aryl H); δ 7.27, dd, 1H (aryl H); δ 7.15, dd, 1H (aryl H); δ 7.03, d, 1H (aryl H); δ 6.97, t, 1H (aryl H); δ 6.91, d, 1H (aryl H); δ 6.65, t, 1H (aryl H); δ 3.83, t, 2H, (CH2 α to O); δ 1.82, t, 2H (CH2 α to COONa); δ 1.3, m, 4H (other two CH2's); δ1.0, m, 6H (CH2's in middle of chain). 13C NMR (d6-DMSO): 198.59, 177.35, 161.35, 156.10, 134.56, 131.98, 131.78, 129.55, 128.57, 123.57, 120.18, 118.00, 117.09, 112.51, 67.74, 37.87, 28.83, 28.35, 28.27, 25.84, 24.87.

Workup

  1. customto precipitate
  2. temperatureHeating this mixture
  3. dissolutionto dissolve
  4. customThe remaining solids were removed by filtration
  5. customThe off-white solid that formed
  6. customwas isolated by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-7921eed0375f46c183206139080bed44
Source dataset
uspto-grants-2012_09
Patent number
US08273794B2

Reaction notes

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