Ethanol → HCID 13298047, compound

HRID 982422Notes

Reaction equation

HRID 982422 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 2 M 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-ef0eeffcfac947daa7bc1705a7ea9574
Source dataset
uspto-grants-1991_02
Patent number
US04996225

Reaction notes

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