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

HRID 67252Notes

Reaction equation

HRID 67252 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-5fabee0300034490aaea844548740f74
Source dataset
uspto-grants-1982_08
Patent number
US04345932

Reaction notes

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