Hydrochloric Acid → HCID 13088563, compound

HRID 67249Notes

Reaction equation

HRID 67249 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:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>N1C=CC=CC=1>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]([O:14][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]([CH3:15])([CH3:16])[C:10]=2[CH:17]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 536079(2-Hydroxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate

Product 1

HCID 13088563HCID 13088563, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled solution of 2-hydroxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (8.0 parts) in dry pyridine (42 parts) was added benzoyl chloride (4.75 parts) at such a rate that the temperature did not exceed 10° C. After one hour the mixture was poured into a slight excess of dilute hydrochloric acid. The product was extracted with ether and the ethereal solution washed, dried with sodium sulphate and evaporated to give an oil which solidified on scratching. The solid was recrystallised from a mixture of benzene and light petroleum to give 2-benzoyloxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (5.1 parts), melting point 102°-104° C.

Workup

  1. customdid not exceed 10° C
  2. extractionThe product was extracted with ether
  3. washthe ethereal solution washed
  4. dry with materialdried with sodium sulphate
  5. customevaporated
  6. customto give an oil which
  7. customThe solid was recrystallised from a mixture of benzene and light petroleum

Sources & evidence

ORD record
ord-e5f165f41b8a43c881a56271e218a452
Source dataset
uspto-grants-1982_08
Patent number
US04345932

Reaction notes

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