Sodium Hydroxide → 4'-Decyloxybiphenyl-4-ylethyne

HRID 442590Notes

Reaction equation

HRID 442590 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25]C(O)(C)C)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 183283931-(4'-Decyloxybiphenyl-4-yl)-2-(1-hydroxy-1-methylethyl)ethyne

Product 1

HCID 183283904'-Decyloxybiphenyl-4-ylethyne

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 73 (12.90 g, 0.033 mol) and sodium hydroxide () was boiled for 1 h in toluene (100 ml) under a dry nitrogen atmosphere and the resultant toluene/acetone mixture removed in a Dean-Stark apparatus. As the toluene mixture was removed fresh toluene was added to the reaction mixture. TLC analysis (dichloromethane) revealed a complete reaction. The sodium hydroxide was filtered off and the toluene washed with water, dried (MgSO4) and removed in vacuo to leave a metallic-beige solid.

Workup

  1. customthe resultant toluene/acetone mixture removed in a Dean-Stark apparatus
  2. customAs the toluene mixture was removed fresh toluene
  3. additionwas added to the reaction mixture
  4. customa complete reaction
  5. filtrationThe sodium hydroxide was filtered off
  6. washthe toluene washed with water
  7. dry with materialdried (MgSO4)
  8. customremoved in vacuo
  9. customto leave a metallic-beige solid

Sources & evidence

ORD record
ord-f64cfff93fe5480bbfc6f48bf0891d64
Source dataset
uspto-grants-1999_04
Patent number
US05891358

Reaction notes

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