Hydrochloric Acid → HCID 21568964, compound

HRID 1579632Notes

Reaction equation

HRID 1579632 reaction equation
[CH3:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:14].[C:15](Cl)(=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH3:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[O:10][C:6]=2[CH:5]=[C:4]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[C:3]=1[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 61186Valeryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21568959HCID 21568959, compound

Product 1

HCID 21568964HCID 21568964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A stirred suspension of 4,5-dimethylbenzofuran-2-carboxylic acid (18 g.) and valeryl chloride (15 g.) in methylene chloride (300 ml.) is cooled to 5°C. and treated with aluminum chloride (40 g.) in portions during a 1/2 hour period during which time the suspended reactant dissolves. The reaction mixture is stirred at 25° for 2 days then poured into ice water (500 ml.) containing hydrochloric acid (50 ml.). The product (21 g.) separates from the biphasic solution, is filtered and recrystallized from ethanol-water affording 4,5-dimethyl-6-valerylbenzofuran-2-carboxylic acid which melts at 188°-9°C.

Workup

  1. dissolutiondissolves
  2. filtrationis filtered
  3. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-3fb557b4d8d1400ab83d4fee4d42d02a
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

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