Thionyl Chloride → 12-Acetoxy-9,10-dihydro-9,10-ethanoanthracene-9-carboxylic acid chloride

HRID 27950Notes

Reaction equation

HRID 27950 reaction equation
[C:1]([O:4][CH:5]1[C:14]2([C:21]([OH:23])=O)[C:15]3[C:20]([CH:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=42)[CH2:6]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:3])[CH3:2].S(Cl)([Cl:26])=O>C1C=CC=CC=1>[C:1]([O:4][CH:5]1[C:14]2([C:21]([Cl:26])=[O:23])[C:15]3[C:20]([CH:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=42)[CH2:6]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1183378712-Acetoxy-9,10-dihydro-9,10-ethanoanthracene-9-carboxylic acid

Product 1

HCID 8874946312-Acetoxy-9,10-dihydro-9,10-ethanoanthracene-9-carboxylic acid chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 12-acetoxy-9,10-dihydro-9,10-ethanoanthracene-9-carboxylic acid (1.0 g) in benzene (10.0 ml) and thionyl chloride (4.0 ml) was refluxed for 4 hours. Evaporation of excess thionyl chloride and benzene gave 12-acetoxy-9,10-dihydro-9,10-ethanoanthracene-9-carboxylic acid chloride. The acid chloride was dissolved in dry acetone (25.0 ml), and a solution of sodium azide (0.63 g) in water (1.3 ml) was added thereto while ice cooling. The resulting mixture was stirred while ice cooling for 2 hours. The reaction mixture was diluted with water and extracted with benzene. The benzene extract was washed with water, dried over anhydrous sodium sulfate, refluxed for 2 hours and evaporated to dryness to give 9-isocyanato-12-acetoxy-9,10-dihydro-9,10-ethanoanthracene.

Workup

  1. customEvaporation of excess thionyl chloride and benzene

Sources & evidence

ORD record
ord-87fa3ea41264420f91408715c993dd38
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Reaction notes

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