Acetic Anhydride → HCID 59806471, compound

HRID 2093238Notes

Reaction equation

HRID 2093238 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:13][CH2:14][C:15]#[CH:16])[CH:12]=1)[CH2:8][OH:9])[C:2]#[CH:3].[C:17](OC(=O)C)(=[O:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[C:17]([O:9][CH2:8][C:7]1[CH:10]=[C:11]([O:13][CH2:14][C:15]#[CH:16])[CH:12]=[C:5]([O:4][CH2:1][C:2]#[CH:3])[CH:6]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 15203944{3,5-Bis[(prop-2-yn-1-yl)oxy]phenyl}methanol

Product 1

HCID 59806471HCID 59806471, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
95 °C

Procedure

3,5-Dipropargyloxybenzyl alcohol (I) (6.3 g, 0.029 mol) was stirred in acetic anhydride (7 mL, 0.07 mol). Concentrated sulfuric acid (2 drops) was added and the solution was stirred (90-100° C.) for 3 hours. The solution was then poured into ice water, neutralized with a saturated sodium carbonate solution and after the reaction was worked up, the product was purified using silica in a sintered glass funnel and the solvents were removed leaving a yellow oil, which solidified upon standing, 7.2 g in 96% yield.

Workup

  1. customthe product was purified
  2. customthe solvents were removed
  3. customleaving a yellow oil, which

Sources & evidence

ORD record
ord-553441f12cb34e3fa160d6f600c488ad
Source dataset
uspto-grants-2013_05
Patent number
US08444953B2

Reaction notes

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