Sulfuric Acid → 2-Acetoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate

HRID 1112121Notes

Reaction equation

HRID 1112121 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([O:14][CH2:15][CH3:16])[C:11]([CH3:18])([CH3:17])[C:10]=2[CH:19]=1)(=[O:4])=[O:3].C(OC(=O)C)(=[O:22])C.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([O:14][C:15](=[O:22])[CH3:16])[C:11]([CH3:18])([CH3:17])[C:10]=2[CH:19]=1)(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 33360EthofumesateHCID 516892Sodium Bicarbonate

Product 1

HCID 130885322-Acetoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate

Procedure

2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (7 parts) was treated with a mixture of acetic anhydride (20 parts) and sulphuric acid (0.6 parts) and left at 50° C. for two hours. The solution was then poured into an excess of ice and sodium bicarbonate. An oil precipitated which solidified and was filtered off and recrystallised from 90, aqueous ethanol to give 2-acetoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (6.6 parts) melting point 83°-85° C.

Workup

  1. customAn oil precipitated which solidified
  2. filtrationwas filtered off
  3. customrecrystallised from 90, aqueous ethanol

Sources & evidence

ORD record
ord-70ed5ba6b1cb4f0fb8c380174c63d5fb
Source dataset
uspto-grants-1978_10
Patent number
US04120871

Reaction notes

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