Acetone → HCID 13264148, compound

HRID 647659Notes

Reaction equation

HRID 647659 reaction equation
[C:1]([C:4]1([OH:22])[CH2:13][C:12]2[C:7](=[C:8]([O:16][CH3:17])[CH:9]=[CH:10][C:11]=2[O:14][CH3:15])[C:6]2([S:21][CH2:20][CH2:19][S:18]2)[CH2:5]1)(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:34][C:35](C)=[O:36].O>C1C=CC=CC=1.C(O)CO.C(OCC)C>[CH2:34]1[CH2:35][O:36][C:1]([C:4]2([OH:22])[CH2:13][C:12]3[C:7](=[C:8]([O:16][CH3:17])[CH:9]=[CH:10][C:11]=3[O:14][CH3:15])[C:6]3([S:21][CH2:20][CH2:19][S:18]3)[CH2:5]2)([CH3:2])[O:3]1

Participants

8

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13264145HCID 13264145, compound

Product 1

HCID 13264148HCID 13264148, compound

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

2.0 g of rac-3'-acetyl-1',2',3',4'-tetrahydro-3'-hydroxy-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] [prepared as described in Example 5(i)] were dissolved in 150 ml of benzene containing 15 ml of ethyleneglycol, 80 mg of toluene-4-sulphonic acid and 5 ml of acetone. The mixture was heated under reflux for 6 hours using a Dean-Stark water separator and then cooled to room temperature. The mixture was washed with two 100 portions of 10% aqueous potassium hydrogen carbonate and two 100 ml portions of water, dried over magnesium sulphate and evaporated to give a white foam. Trituration with diethyl ether gave rac-3'-(1,1-ethylenedioxyethyl)-1',2',3',4'-tetrahydro-3'-hydroxy-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] in the form of colourless crystals of melting point 162.5°-163° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. washThe mixture was washed with two 100 portions of 10% aqueous potassium hydrogen carbonate and two 100 ml portions of water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto give a white foam

Sources & evidence

ORD record
ord-a108510ab7a447dd813cc560b68cf812
Source dataset
uspto-grants-1983_10
Patent number
US04409391

Reaction notes

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