Benzene → 2-Nitrobenzyl hexadecanesulfonate

HRID 649706Notes

Reaction equation

HRID 649706 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].C1C=CC=CC=1.[CH2:18]([S:34](Cl)(=[O:36])=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(N(CC)CC)C>[CH2:18]([S:34]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:36])=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 241BenzeneHCID 119232-Nitrobenzyl alcoholHCID 969231-Hexadecanesulfonyl chloride

Product 1

HCID 150954112-Nitrobenzyl hexadecanesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 7.65 g (0.05 mol) of 2-nitrobenzyl alcohol in 75 ml of benzene containing 5.05 g (0.05 mol) of triethylamine was added 16.25 g (0.05 mol of hexadecanesulfonyl chloride. The mixture was stirred an additional four hours. The mixture was evaporated to dryness in vacuo and the solid taken up into a mixture of ether and water. The ether layer was separated and dried over MgSO4. Evaporation of the ether gave a solid which was crystallized from absolute ethanol (yield 14.3 g, m.p. 63°-65° C.).

Workup

  1. customThe mixture was evaporated to dryness in vacuo
  2. additionthe solid taken up into a mixture of ether and water
  3. customThe ether layer was separated
  4. dry with materialdried over MgSO4
  5. customEvaporation of the ether
  6. customgave a solid which
  7. customwas crystallized from absolute ethanol (yield 14.3 g, m.p. 63°-65° C.)

Sources & evidence

ORD record
ord-279744f9a4f14cb39654d967c3e65756
Source dataset
uspto-grants-1988_04
Patent number
US04740600

Reaction notes

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