Acetic Anhydride → HCID 13561791, compound

HRID 1380373Notes

Reaction equation

HRID 1380373 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][CH2:15][CH:16]([OH:18])[CH3:17].[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([O:18][CH:16]([CH2:15][CH2:14][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:12][C:13]=2[CH:1]=1)[CH3:17])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13561783HCID 13561783, compound

Product 1

HCID 13561791HCID 13561791, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 4.72 grams of 4-(2-fluorenyl)-butan-2-ol were added 1.74 grams of pyridine and 2.24 grams of acetic anhydride and the mixture was heated to reflux for 25 hours. An excess of acetic anhydride and pyridine was removed by evaporation, the residue was subjected to a silica gel column chromatography, the column was eluted with a 4:1 mixture of n-hexane and ethyl acetate, and the resulting crystals were recrystallized from n-hexane to give 5 grams of 4-(2-fluorenyl)-butan-2-ol acetate, white crystals, m.p. 63°-64.5° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 25 hours
  3. customAn excess of acetic anhydride and pyridine was removed by evaporation
  4. washthe column was eluted with a 4:1 mixture of n-hexane and ethyl acetate
  5. customthe resulting crystals were recrystallized from n-hexane

Sources & evidence

ORD record
ord-4c05c73b92aa4274bcc4381a07b7de78
Source dataset
uspto-grants-1986_04
Patent number
US04581377

Reaction notes

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