Water → HCID 13298064, compound

HRID 982440Notes

Reaction equation

HRID 982440 reaction equation
C(O[CH:4]([O:36]CC)[CH2:5][CH:6]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:11][CH:10]=1)[OH:8])C.S(=O)(=O)(O)O.O.[OH-].[Na+]>O1CCCC1>[OH:36][CH:4]1[O:8][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[CH:13][CH:14]=2)[CH:6]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 20067699HCID 20067699, compound

Product 1

HCID 13298064HCID 13298064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The evaporation residue obtained in step (a) is dissolved in a mixture containing 19.5 g of concentrated sulfuric acid, 150 ml of water and 400 ml of tetrahydrofuran. The mixture is stirred for 3 h at room temperature. The solution is neutralized with 2 M sodium hydroxide solution and the solvent is evaporated. The product is extracted in toluene containing ethyl acetate. The solution is dried over sodium sulfate. The solvent is evaporated, and the residue is recrystallized from toluene. The yield is 12.0 g (27% from desoxybenzoin) of a product having m.p. 150°-3° C.

Workup

  1. customthe solvent is evaporated
  2. extractionThe product is extracted in toluene
  3. additioncontaining ethyl acetate
  4. dry with materialThe solution is dried over sodium sulfate
  5. customThe solvent is evaporated
  6. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-4f9aa305cf3f475eab01f34154bd9822
Source dataset
uspto-grants-1991_02
Patent number
US04996225

Reaction notes

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