Potassium Hydroxide → HCID 22154304, compound

HRID 2057411Notes

Reaction equation

HRID 2057411 reaction equation
C[O:2][C:3](=[O:16])[CH:4]=[C:5]1[C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1.[H][H].COC(=O)CC1C2C=C(Cl)C=CC=2OCC1.[OH-].[K+]>[Pd].C.C(OCC)(=O)C.O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]2[O:8][CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:16])=[O:2])[C:10]=2[CH:11]=1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 54092764HCID 54092764, compoundHCID 54437452HCID 54437452, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22154304HCID 22154304, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 14818447PalladiumcarbonCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-chloro-3,4-dihydro-2H-1-benzpyran-4-ylidene-acetic acid methyl ester (2.0 g.) was reduced with hydrogen using a 10% Pd-charcoal catalyst (0.20 g.) by stirring at 25° C. in ethyl acetate for 4 hours. The reduction product, 6-chloro-3,4-dihydro-2H-1-benzopyran-4-acetic acid methyl ester (1.0 g.), was heated for 3 days at reflux temperature with potassium hydroxide (2.4 g.) in 25 ml. water. The solution was acidified and extracted with chloroform. Recrystallization from cyclohexane gave 6-chloro-3,4-dihydro-2H-1-benzopyran-4-acetic acid (650 mg. 60%), m.p. 115°-117° C.

Workup

  1. extractionextracted with chloroform
  2. customRecrystallization from cyclohexane

Sources & evidence

ORD record
ord-88265a3232644f9b95beb61e562b9093
Source dataset
uspto-grants-1980_07
Patent number
US04210663

Reaction notes

Loading…