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

HRID 2072309Notes

Reaction equation

HRID 2072309 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].C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>CCOCC>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([O:14][C:25](=[O:27])[CH3:26])[C:11]([CH3:15])([CH3:16])[C:10]=2[CH:17]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 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 3283Diethyl EtherSolvent

Procedure

A solution of 2-hydroxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (5 parts) in ether (85 parts) was treated with triethylamine (2.2 parts) and acetic anhydride (2.3 parts) at 10° C and allowed to stand for 4 hours. The solution was then diluted with light petroleum (80 parts) and filtered. The filtrate was evaporated to give an oil which solidified. This was recrystallised from a mixture of chloroform and petroleum to give 2-acetoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (2.5 parts), melting point 84°-85° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customto give an oil which
  4. customThis was recrystallised from a mixture of chloroform and petroleum

Sources & evidence

ORD record
ord-2000748381d04dc59d6d325c5e4551cc
Source dataset
uspto-grants-1977_09
Patent number
US04051154

Reaction notes

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