Hydrochloric Acid → 4-(2-phenylethynyl)phenol

HRID 1492663Notes

Reaction equation

HRID 1492663 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.N1C(C)=CC(C)=CC=1C.[Li+].[I-].Cl>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[C:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 66321Lithium iodideHCID 6104021-Methoxy-4-(phenylethynyl)benzene

Product 1

HCID 110088074-(2-phenylethynyl)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure similar to that described1 was used. A sample of 1-methoxy-4-(phenylethynyl)-benzene (0.4 g, 1.9 mmol) was added collidine (3 mL), LiI (1.5 g) and the solution heated under reflux for 5 h (>95% conversion). The solution was poured into water acidified with HCl, extracted with ether (3×50 mL) and dried (MgSO4). The ether was evaporated and the residue chromatographed (PE) eluting the title compound 0.3 g (80%): mp 125°-128° C. (cyclohexane) (lit2 mp 91°-92° C., lit3 mp 83°-84° C.); 1H NMR (300 MHz, DMSO-d6) δ6.80 (d, J=8.77 Hz, 2H, C2H), 7.37 (d, 2H, C3H), 7.35-7.42 (m, 3H), 7.46-7.50 (m, 2H), 9.92 (s, 1H, OH); 13C NMR (300 MHz, DMSO-d6 ) δ87.32 (acetylenic C), 89.98 (acetylenic C), 112.42 (sp2C), 115.74, 122.90 (sp2C), 128.20, 128.66, 131.06, 133.00, 158.06 (COH); IR (CDCl3) 3596 (OH), 3066 (w), 3039 (w), 2217 (w, acetylenic stretch), 1605, 1512, 1429 (w), 1328 (w), 1261 (s), 1219, 1171 (s), 1140 (w), 1099 (w), 834, 805 (w) cm-1. MS (El) m/e 194 (M+, 100), 165 (29.4), 97 (11.3).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 5 h (>95% conversion)
  3. extractionextracted with ether (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. customThe ether was evaporated
  6. customthe residue chromatographed (PE)
  7. washeluting the title compound 0.3 g (80%)

Sources & evidence

ORD record
ord-755da1d4072042358141b43c45bb9301
Source dataset
uspto-grants-1994_12
Patent number
US05374701

Reaction notes

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