Potassium Carbonate → Tert-butyl 4-ethynylbenzoate

HRID 974208Notes

Reaction equation

HRID 974208 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si](C)(C)C)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:8]=[CH:9][C:10]([C:13]#[CH:14])=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 13965007tert-Butyl 4-((trimethylsilyl)ethynyl)benzoate

Product 1

HCID 13965008Tert-butyl 4-ethynylbenzoateYield 95.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

274.4 g of 4-(trimethylsilylethinyl)-benzoic acid tert.-butyl ester and 12.5 g of anhydrous potassium carbonate in 1.5 l of absolute methanol are stirred together for 3 hours under nitrogen. The reaction mixture is then concentrated by evaporation and worked up with CH2Cl2 /H2O to yield 194 g of 4-ethinyl-benzoic acid tert.-butyl ester.

Workup

  1. concentrationThe reaction mixture is then concentrated by evaporation

Sources & evidence

ORD record
ord-39fd856448a04295a5c1912c3375a7ac
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

Loading…