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Trityl chloride → 1,1,1-Triphenyl-2,5,8,11-tetraoxatridecan-13-OL

HRID 1818094
Notes
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Reaction equation

HRID 1818094 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].C(N(CC)CC)C.[C:21]1([C:27](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[C:21]1([C:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8200Tetraethylene GlycolHCID 8471Triethylamine

Product 1

HCID 115465991,1,1-Triphenyl-2,5,8,11-tetraoxatridecan-13-OLYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To tetraethylene glycol (213.65 g, 1.1 mol) and triethylamine (20.24 g, 27.8 ml, 200 mmol) in dry dichloromethane (1500 ml) was added dropwise triphenylmethyl chloride (27.88 g, 100 mmol) in dry dichloromethane (500 ml). This solution was left to stir under argon at room temperature for 24 hours. After 24 hours, the reaction was concentrated in vacuo to give a mixture of product and starting material as a yellow oil. This oil was then re-dissolved in dichloromethane (1000 ml), partitioned with sat. aq. NaHCO3 (500 ml), water (3×400 ml) and finally sat. aq. NaCl (500 ml). The organic layer was separated, dried over anhydrous sodium sulphate and concentrated in vacuo to give the title compound as a yellow oil (42.2 g, 95%) which was used without further purification.

Workup

  1. waitThis solution was left
  2. waitAfter 24 hours
  3. concentrationthe reaction was concentrated in vacuo
  4. customto give
  5. additiona mixture of product
  6. custompartitioned with sat. aq. NaHCO3 (500 ml), water (3×400 ml) and finally sat. aq. NaCl (500 ml)
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-280a06e1faf14c1bb73f514356487fe8
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07598421B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes