Hydrochloric Acid → HCID 21419712, compound

HRID 441673Notes

Reaction equation

HRID 441673 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]2[C:8](=[O:18])[C:9]3[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:10]=3[CH2:11][CH2:12][C:6]=2[CH:5]=1)([OH:3])=[O:2].[OH-].[K+].[CH:23](Br)([CH3:25])[CH3:24].Cl>C(O)C.O>[C:1]([C:4]1[CH:20]=[CH:19][C:7]2[C:8](=[O:18])[C:9]3[CH:16]=[C:15]([O:17][CH:23]([CH3:25])[CH3:24])[CH:14]=[CH:13][C:10]=3[CH2:11][CH2:12][C:6]=2[CH:5]=1)([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 21419717HCID 21419717, compound

Product 1

HCID 21419712HCID 21419712, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

0.82 G. of 2-carboxy-7-hydroxy-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene was dissolved in 30 ml of ethanol and a solution of 1.0 g of potassium hydroxide in 5 ml of water was added, followed by 2.0 ml of isopropyl bromide. The reaction was refluxed for 3 hours, then diluted with water and acidified with dilute hydrochloric acid. The product was filtered off and recrystallized from aqueous dimethylformamide to give 2-carboxy-7-isopropoxy-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene, m.p. 174°-177°. By substituting other alkylbromides or iodides such as ethyl bromide, m-propyl bromide, isobutyl bromide, n-amyl bromide, n-hexyl bromide and the like, the corresponding 2-carboxy-7-alkoxy-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptenes are obtained. The 8- and 9- alkoxy compounds are similarly prepared.

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. filtrationThe product was filtered off
  3. customrecrystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-919c30fc7ec84153ba8992437225144c
Source dataset
uspto-grants-1977_08
Patent number
US04041173

Reaction notes

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