Trityl chloride → 4-trityloxybutan-1-ol

HRID 234213Notes

Reaction equation

HRID 234213 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[C:7]1([C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>N1C=CC=CC=1>[C:13]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 80641,4-Butanediol

Product 1

HCID 3717024-trityloxybutan-1-olYield 41.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 45 g of butane-1,4-diol in 0.25 of pyridine, cooled to 0° C., were added 139.4 g of triphenylchloromethane and the mixture was stirred at room temperature for 26 h. The precipitate formed was removed by filtration and the filtrate was evaporated in vacuo. The residue was taken up in 0.5 l of ethyl acetate and the solution was washed successively with 200 ml portions of water, 1N hydrochloric acid, water, 5% sodium bicarbonate solution and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. Crystallization of the residual material from ethyl acetate/hexane afforded 69.0 g of 4-trityloxy-1-butanol as white crystals of m.p. 73°-74° C.

Workup

  1. customThe precipitate formed
  2. customwas removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. washthe solution was washed successively with 200 ml portions of water, 1N hydrochloric acid, water, 5% sodium bicarbonate solution and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customCrystallization of the residual material from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e9af9902f91548aa823d4c01ddcf9eaa
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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