Carbon Dioxide → Benzoic acid, 2,6-dihydroxy-4-pentyl-

HRID 488670Notes

Reaction equation

HRID 488670 reaction equation
[C:1]1([OH:13])[CH:12]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:3]([OH:4])[CH:2]=1.[C:14](=[O:16])=[O:15]>OCC(CO)O>[OH:13][C:1]1[CH:12]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:3]([OH:4])[C:2]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 10377Olivetol

Product 1

HCID 3046173Benzoic acid, 2,6-dihydroxy-4-pentyl-

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

A mixture of olivetol (2.1 g, 12 mM), KHCO3 (4.9 g, 39 mM), and solid CO2 (1.95 g, 44.3 mM) in glycerol (5.1 mL) was heated in a stainless steel bomb to 145° C. at 220 psi for 5 hours. The reaction was cooled and removed from the reaction vessel using water to transfer. The aqueous solution was carefully acidified to a pH=3 with 1 N HCl to give a precipitate. The solids were filtered, washed with water and dried to give the desired product. MS (ESI(−)) m/e 223 (M−H)+; 1H NMR (300 MHz, CDCl3) δ 9.40 (bs, 2H), 6.37 (s, 2H), 2.52 (t, 2H), 1.66-1.57 (m, 2H), 1.37-1.29 (m, 4H), 0.93-0.87 (m, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. customremoved from the reaction vessel
  3. customto give a precipitate
  4. filtrationThe solids were filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5a7ed312a06443b2894a68a7ac61effa
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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