Acetylene → HCID 12848144, compound

HRID 2188320Notes

Reaction equation

HRID 2188320 reaction equation
[CH2:1]([B:8]([Cl:10])Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C#C.C(=O)=O.[CH3:16][C:17](C)=O.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:10][B:8]1[CH:17]=[CH:16][C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:1]1

Participants

7

Reactant 4

HCID 6326Acetylene3×HCID 14798Sodium HydroxideHCID 12848123HCID 12848123, compoundHCID 18522661Acetone cardice

Product 1

HCID 12848144HCID 12848144, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

About 10.0 ml (11.51 grams, 66.6 mmoles) of benzyl dichloroborane is dissolved in 100 ml of toluene in a 500 ml three-neck flask. Research grade acetylene is passed at a rate of 100 ml STP/min through two dry ice/acetone traps and a column (10 inches long ×1 inch ID) of activated basic alumina. The acetylene is introduced into the stirring solution through a needle below the surface of the liquid. The flask is vented to a scrubber containing 2.7 grams of NaOH in 1500 ml of water. The reaction is allowed to proceed for 3 hours. The acetylene flow is stopped and the volatiles in the reaction flask are evaporated under vacuum. 10.37 grams of colorless product are recovered. This is identified as 2-chloro-1,2-dihydro-2-boranaphthalene by NMR. This product is used in subsequent steps without further purification. The yield is 95 %.

Workup

  1. customthe volatiles in the reaction flask are evaporated under vacuum
  2. custom10.37 grams of colorless product are recovered
  3. customThis product is used in subsequent steps without further purification

Sources & evidence

ORD record
ord-50bc6b4002d343ff8a73c5477af0633f
Source dataset
uspto-grants-2002_06
Patent number
US06410764B1

Reaction notes

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