Trifluoroacetic acid → (rac)-1-O-dodecyl-2-O-methoxycarbonyl-glycerol

HRID 2412547Notes

Reaction equation

HRID 2412547 reaction equation
[CH2:1]([O:13][CH2:14][CH:15]([CH2:21][O:22]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:16][C:17]([O:19][CH3:20])=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:13][CH2:14][CH:15]([CH2:21][OH:22])[O:16][C:17]([O:19][CH3:20])=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54191648(rac)-1-O-dodecyl-2-O-methoxycarbonyl-3-O-trityl-glycerol

Product 1

HCID 53790783(rac)-1-O-dodecyl-2-O-methoxycarbonyl-glycerolYield 107.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (rac)-1-O-dodecyl-2-O-methoxycarbonyl-3-O-trityl-glycerol (10.2 g) in methylene chloride (100 ml) was added trifluoroacetic acid (10 ml) in one portion. After the yellow solution was stirred for 8 minutes at ambient temperature, ice water (100 ml) was added. The organic layer was washed with aqueous sodium bicarbonate solution and water, dried, and evaporated under reduced pressure. The residue was treated with n-hexane (50 ml) to remove triphenylmethanol as a white crystal. The filtrate was evaporated to give 6.22 g of (rac)-1-O-dodecyl-2-O-methoxycarbonyl-glycerol as a colorless oil (unstable oil).

Workup

  1. washThe organic layer was washed with aqueous sodium bicarbonate solution and water
  2. customdried
  3. customevaporated under reduced pressure
  4. additionThe residue was treated with n-hexane (50 ml)
  5. customto remove triphenylmethanol as a white crystal
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-6a12966c9e16492c899c5d05c52b8666
Source dataset
uspto-grants-1985_01
Patent number
US04493832

Reaction notes

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