Water → (2-Hydroxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate

HRID 67248Notes

Reaction equation

HRID 67248 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12](N3CCOCC3)[C:11]([CH3:21])([CH3:20])[C:10]=2[CH:22]=1)(=[O:4])=[O:3].[OH2:23]>Cl>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([OH:23])[C:11]([CH3:21])([CH3:20])[C:10]=2[CH:22]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 962WaterHCID 13088513HCID 13088513, compound

Product 1

HCID 536079(2-Hydroxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 2,3-dihydro-3,3-dimethyl-2-morpholinobenzofuran-5-yl methanesulphonate (product of Example 2) (24.9 parts) in water (50 parts) and hydrochloric acid (22.4 parts) was rapidly heated to 90°-100° C. and then cooled after 2 minutes. The crude product was extracted into ether (3×60 parts) and the extracts washed with water (2×50 parts), dried with sodium sulphate and evaporated to leave a gum which crystallised to give 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran-5-yl methanesulphonate, m.p. 69°-72° C. (16 parts)

Workup

  1. temperaturewas rapidly heated to 90°-100° C.
  2. temperaturecooled after 2 minutes
  3. extractionThe crude product was extracted into ether (3×60 parts)
  4. washthe extracts washed with water (2×50 parts)
  5. dry with materialdried with sodium sulphate
  6. customevaporated
  7. customto leave a gum which
  8. customcrystallised

Sources & evidence

ORD record
ord-cd5f8986fa0a4751835d00b0973384c8
Source dataset
uspto-grants-1982_08
Patent number
US04345932

Reaction notes

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