Acetic Anhydride → HCID 21503923, compound

HRID 1077306Notes

Reaction equation

HRID 1077306 reaction equation
[CH2:1]([C:5]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)[CH2:2][CH2:3][CH3:4].C(C1C=CC2C3C(=CC=CC=3)CC=2C=1)C.[C:33](OC(=O)C)(=[O:35])[CH3:34].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[C:33]([C:11]1[CH:12]=[CH:13][C:14]2[C:15]3[C:7](=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:17][CH:16]=3)[CH2:8][C:9]=2[CH:10]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 2749392-Ethyl-9H-fluoreneHCID 6451240Aluminum(III) ChlorideHCID 21503899HCID 21503899, compound

Product 1

HCID 21503923HCID 21503923, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-Butylfluorene (6.1 g.) was acetylated exactly as described for 2-ethylfluorene in the preceding Example 21, using acetic anhydride (3.08 g.) and aluminium chloride (8.66 g.) in dichloroethane. The product was recrystallised from light petroleum to give 2-acetyl-7-butylfluorene, m.p. 102°-104.5°. This product (1.98 g.) was oxidised with sodium hypobromite (from 7.23 g. of bromine and 4.52 g. sodium hydroxide in 160 ml. water) exactly as described for 2-acetyl-7-ethylfluorene in the preceding Example. The 7-butylfluorenone-2-carboxylic acid thus isolated had m.p. > 300° and was homogeneous by thin layer chromatography.

Workup

  1. customThe product was recrystallised from light petroleum

Sources & evidence

ORD record
ord-6b102e6e31f6401fbd8b3e0a86ff4063
Source dataset
uspto-grants-1976_05
Patent number
US03959482

Reaction notes

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