Potassium Carbonate → 4-Methoxymethoxy-2-methylbenzofuran

HRID 485182Notes

Reaction equation

HRID 485182 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][O:20][CH3:21]>CC(C)=O>[CH3:19][O:20][CH2:21][O:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 83093Bromomethyl methyl etherHCID 121745614-Hydroxy-2-methylbenzofuran

Product 1

HCID 202715384-Methoxymethoxy-2-methylbenzofuran

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 4-hydroxy-2-methylbenzofuran (7.1 g, 0.048 M), anhydrous powdered potassium carbonate (19.87 g) and acetone (82 ml), was added dropwise bromomethoxymethane (11.99 g, 7.88 ml, 0.0959 M) with ice cooling. After the addition was complete the reaction mixture was stirred at room temperature overnight, filtered and evaporated. The residual oil was distilled to give 4-methoxymethoxy-2-methylbenzofuran, b.p. 94°-97° C./0.8 mmHg.

Workup

  1. additionAfter the addition
  2. filtrationfiltered
  3. customevaporated
  4. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-1fd681e384df4986b02f7f0308cedf9a
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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