Acetic Anhydride → 2-Acetoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate

HRID 67251Notes

Reaction equation

HRID 67251 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([OH:14])[C:11]([CH3:16])([CH3:15])[C:10]=2[CH:17]=1)(=[O:4])=[O:3].[OH-].[Na+].[C:20](OC(=O)C)(=[O:22])[CH3:21]>O>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([O:14][C:20](=[O:22])[CH3:21])[C:11]([CH3:15])([CH3:16])[C:10]=2[CH:17]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 536079(2-Hydroxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-hydroxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (10 parts) in water (100 parts) containing sodium hydroxide (15 parts) was slowly added acetic anhydride (10 parts) with cooling to keep the temperature below 10° C. An oil separated which solidified on scratching. This was filtered off, washed with water, dried and recrystallised from 90% aqueous ethanol to give 2-acetoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate, melting point 84°-85° C.

Workup

  1. temperaturewith cooling
  2. customthe temperature below 10° C
  3. customAn oil separated which
  4. filtrationThis was filtered off
  5. washwashed with water
  6. customdried
  7. customrecrystallised from 90% aqueous ethanol

Sources & evidence

ORD record
ord-009763b1a6e54d6cab120dbee9edb01a
Source dataset
uspto-grants-1982_08
Patent number
US04345932

Reaction notes

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