Methanol → HCID 12812398, compound

HRID 848196Notes

Reaction equation

[H-].[Na+].Cl[CH:4](Cl)[C:5]([OH:7])=[O:6].[OH:9][C:10]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:11]=1[C:12]([CH3:20])([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CO>O1CCOCC1.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:10]2[O:9][CH:4]([C:5]([OH:7])=[O:6])[O:19][C:12]([CH3:20])([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:11]=2[CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

60 mg of dibenzo-18-couronne-6 were added at 150° C. to a mixture of 10 ml of dioxane and 1.35 g of sodium hydride as a 50% oil suspension and then a solution of 0.61 ml of dichloroacetic acid in 10 ml of dioxane was added thereto over 5 minutes followed by addition of solution of 1.25 g of 2-hydroxy-5-chloro-α-methyl-benzhydrol in 5 ml of dioxane over 10 minutes at 20° C. The mixture was heated for 6 hours at 80° C., cooled to 20° C. and 2 ml of methanol were added thereto. The mixture was poured into iced water and was extracted three times with ethyl acetate. The organic extracts were washed 5 times with 0.1 N sodium hydroxide and the combined aqueous phases were acidified to a pH of 1 with 2 N hydrochloric acid and extracted 3 times with methylene chloride. The organic extracts were dried and evaporated to dryness to obtain raw 6-chloro-4-methyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid (mixture of two racemates diastereoisomers).

Workup

temperaturecooled to 20° C.
extractionwas extracted three times with ethyl acetate
washThe organic extracts were washed 5 times with 0.1 N sodium hydroxide
extractionextracted 3 times with methylene chloride
customThe organic extracts were dried
customevaporated to dryness

Sources & evidence

ORD record: ord-dee949e3cd6746e88b6e307739432fa2
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04294845

Reaction notes

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