Ethanol → HCID 13298047, compound

HRID 2309759Notes

Reaction equation

HRID 2309759 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH:10]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12].C(O)C.S(=O)(=O)(O)O.[OH-].[Na+]>O>[C:19]1([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([OH:12])[CH:10]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:9][CH2:8][OH:7])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13298046HCID 13298046, compound

Product 1

HCID 13298047HCID 13298047, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The evaporation residue obtained in step (b) is dissolved in a mixture containing 400 ml of absolute ethanol, 10 g of concentrated sulfuric acid and 75 ml of water. The mixture is stirred for 2 h at room temperature. The solution is neutralized with 2M sodium hydroxide solution, after which the ethanol is evaporated. Water is added to the residue. Then the product is extracted in ethyl acetate. The ethyl acetate solution is dried over sodium sulfate, and the solvent is evaporated. The product is recrystallized from toluene. The yield is 16.5 g (52% from desoxybenzoin) and m.p. 185°-7° C.

Workup

  1. customafter which the ethanol is evaporated
  2. additionWater is added to the residue
  3. extractionThen the product is extracted in ethyl acetate
  4. dry with materialThe ethyl acetate solution is dried over sodium sulfate
  5. customthe solvent is evaporated
  6. customThe product is recrystallized from toluene

Sources & evidence

ORD record
ord-6e753ec7b01e451d9e1c99ff9bd842e9
Source dataset
uspto-grants-1987_09
Patent number
US04696949

Reaction notes

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