Hydrochloric Acid → 1-(3-Hydroxyphenyl)-oct-1-yne

HRID 256001

Reaction equation

HRID 256001 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]=[CH:7][CH:8]=1.[I-].[Li+].O.Cl>N1C(C)=CC(C)=CC=1C>[OH:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 66321Lithium iodideHCID 112644061-Methoxy-3-(1-octynyl)benzene

Product 1

HCID 135002601-(3-Hydroxyphenyl)-oct-1-yne

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

1-(3-Methoxyphenyl)-oct-1-yne, (6.50 g, 0.03M), was dissolved in 2,4,6-collidine, (100 ml), and anhydrous lithium iodide (20.08 g, 0.15M), added. The reaction was stirred under nitrogen at reflux temperature for 48 h, then cooled and poured intro water, (500 ml), and acidified with dilute hydrochloric acid. The product was extracted into ethyl acetate, (twice), and the organic phases combined, washed with water (twice) and dried, (MgSO4). Evaporation of the solvent in vacuo yielded the crude product as a brown oil, which was purified by chromatography on silica gel, eluting with dichloromethane/n-hexane [1:1] to chloroform. 5.40 g (90%) of product was collected as a colourless oil. νmax (film) 1580, 1590, 1605, 2230 (weak) 3400 cm-1 ; δ(CDCl3) 0.85 (3H, distorted t, terminal CH3), 1.39 (8H, m, alkylene chain), 2.32 (2H, t, J 6 Hz, acetylenic CH2), 4.77 (1H, s, OH, exchanged with D2O), 6.78 (2H, m, aromatics), 7.02 (2H, m, aromatics).

Workup

  1. temperatureat reflux temperature for 48 h
  2. temperaturecooled
  3. extractionThe product was extracted into ethyl acetate
  4. washwashed with water (twice) and
  5. customdried
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-262448fd7514495bb44c9f9b3a4dd240
Source dataset
uspto-grants-1987_10
Patent number
US04699995

Linked notes

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