Hydrochloric Acid → 1-Chloro-2-ethynylbenzene

HRID 556336Notes

Reaction equation

HRID 556336 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][Si](C)(C)C.C(OCC)(=O)C.Cl>CO.CCCCCC>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[CH:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 13572894HCID 13572894, compound

Product 1

HCID 5859951-Chloro-2-ethynylbenzeneYield 65.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Potassium hydroxide (77.5 g, 1.38 mol) was added in 4 portions to a stirred solution of (2-chlorophenylethynyl)-trimethylsilane (95.0 g, 0.46 mol) in methanol (250 ml) at 0° C. The mixture was stirred at 0° C. until the reaction was complete (by tlc 1:1 ethyl acetate:hexane). The mixture was neutralised by the addition of 10% hydrochloric acid and the product was extracted into dichloromethane (2×150 ml). The combined extracts were dried (MgSO4) and evaporated in vacuo. The residual oil was purified by short path distillation (Kugelrohr) to give 1-chloro-2-ethynylbenzene (41.23 g) as a clear oil. B.pt. 38° C./10 mBar. 250 MHz 1H-NMR (CDCl3) δ (ppm): 3.25 (s, 1H)(CH), 7.1-7.5 (m, 4H) (ArH); GC purity 89%, GC retention time 2.67 min.

Workup

  1. extractionthe product was extracted into dichloromethane (2×150 ml)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated in vacuo
  4. distillationThe residual oil was purified by short path distillation (Kugelrohr)

Sources & evidence

ORD record
ord-d40ca3a0d38d4b438e49ce3da58ba2fd
Source dataset
uspto-grants-2011_11
Patent number
US08058283B2

Reaction notes

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