Trityl chloride → HCID 19866545, compound

HRID 255967Notes

Reaction equation

HRID 255967 reaction equation
[CH2:1]([O:17][CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:24](Cl)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[CH2:1]([O:17][CH2:18][CH2:19][CH:20]([OH:23])[CH2:21][O:22][C:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 13959073HCID 13959073, compound

Product 1

HCID 19866545HCID 19866545, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 30 g of 4-(hexadecyloxy)-1,2-butanediol in 135 ml of dry pyridine was added 37.95 g of trityl chloride. The solution was allowed to stand under argon for 24 hours and was then poured into 700 ml of ice water and extracted three times with ether. The ether extracts were combined, washed with ice cold 5% hydrochloric acid, then saturated salt solution, dried and evaporated to dryness. The residue was mixed with petroleum ether, allowed to stand 72 hours, the solid removed and the mother liquor taken to dryness, giving 56.65 g of the desired compound as an oil.

Workup

  1. extractionextracted three times with ether
  2. washwashed with ice cold 5% hydrochloric acid
  3. customsaturated salt solution, dried
  4. customevaporated to dryness
  5. additionThe residue was mixed with petroleum ether
  6. waitto stand 72 hours
  7. customthe solid removed

Sources & evidence

ORD record
ord-3e260ac7fc20424fb082eac6c017a074
Source dataset
uspto-grants-1987_10
Patent number
US04699990

Reaction notes

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