Triethylamine → HCID 131718071, compound

HRID 2254653Notes

Reaction equation

HRID 2254653 reaction equation
ClC[C:3]([C:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([OH:9])C(Cl)=O)=[O:4].[CH3:16][CH:17]([CH2:19][CH2:20][CH2:21][C@H:22]([CH2:24][CH2:25][CH2:26][C@H:27]([CH2:29][CH2:30][CH2:31]/[C:32](=[CH:34]/[CH2:35][OH:36])/[CH3:33])[CH3:28])[CH3:23])[CH3:18].C(N(CC)CC)C.NC(N)=S>C(Cl)Cl.CO.C(OCC)(=O)C>[C:3]([O:36][CH2:35]/[CH:34]=[C:32](/[CH2:31][CH2:30][CH2:29][C@@H:27]([CH2:26][CH2:25][CH2:24][C@@H:22]([CH2:21][CH2:20][CH2:19][CH:17]([CH3:16])[CH3:18])[CH3:23])[CH3:28])\[CH3:33])(=[O:4])[CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9]

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 2723790ThioureaHCID 5280435PhytolHCID 54344361HCID 54344361, compound

Product 1

HCID 131718071HCID 131718071, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

10 ml of a methylene chloride solution containing 10.0 g of chloroacetylmandelic acid chloride was dropped into a solution of 10.0 g of phytol and 4.5 g of triethylamine dissolved in 30 ml of methylene chloride at 30°-40° C. The resulting mixture was stirred for 2 hours at the same temperature. After the completion of the reaction, the reaction mixture was washed with dilute hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order. The solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in 50 ml of methanol. Thereto were added 3.8 g of triethylamine and 2.9 g of thiourea at room temperature. The resulting mixture was stirred for 3 hours at the same temperature. After the completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in ethyl acetate and the resulting solution was washed with dilute hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant; n-hexane:ethyl acetate=9:1) to obtain 13.0 g (yield: 90%) of oily phytyl mandelate.

Workup

  1. customAfter the completion of the reaction
  2. washthe reaction mixture was washed with dilute hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order
  3. customThe solvent was removed by distillation under reduced pressure
  4. customThe residue obtained
  5. stirringThe resulting mixture was stirred for 3 hours at the same temperature
  6. customAfter the completion of the reaction
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue obtained
  9. washthe resulting solution was washed with dilute hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customThe residue obtained
  13. customwas purified by a column chromatography (eluant; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-55dcf1cb65784226ae18adeaa3d46074
Source dataset
uspto-grants-1993_08
Patent number
US05236950

Reaction notes

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