Water → HCID 19700523, compound

HRID 861846Notes

Reaction equation

HRID 861846 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([C:14]([OH:21])([CH2:19][CH3:20])[C:15]#[C:16][CH2:17][OH:18])[CH3:13].[OH-].[K+].O>CCOCC>[CH2:12]([C:14]([OH:21])([C:15]#[C:16][CH2:17][O:18][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:19][CH3:20])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 211888734-Ethylhex-2-yne-1,4-diol

Product 1

HCID 19700523HCID 19700523, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An ice-cold solution of 4-toluenesulfonyl chloride (6.4 g) and 4-ethylhex-2-yn-1,4-diol (McLamore, W. M. et al., J. Org. Chem., 19, 570-574 (1954) and Gouge, M., Ann. Chim., 6, 648-702 (1951)) (4.0 g) in ether (40 ml) was stirred with powdered potassium hydroxide (15 g) for 2 h. Water was added and the mixture was extracted with ether (2×250 ml). Work-up with chromatography using ether/pentane 1:1 (v/v) gave the title compound (6.5 g). 1H NMR: 0.91 (t, 6H), 1.55 (q, 4H), 1.83 (s, 1H), 2.45 (s, 2H), 4.76 (s, 2H), 7.36 (d, 2H), 7.82 (d, 2H).

Workup

  1. extractionthe mixture was extracted with ether (2×250 ml)

Sources & evidence

ORD record
ord-0a195cedb64d4afd83ca29185a29f2b9
Source dataset
uspto-grants-1998_02
Patent number
US05716945

Reaction notes

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