Acetic Acid → Hydrochloric Acid

HRID 2057408Notes

Reaction equation

HRID 2057408 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8]C(C#N)(O[Si](C)(C)C)[C:6]=2[CH:18]=1.[C:19]([OH:22])(=[O:21])[CH3:20]>>[ClH:1].[Cl:1][C:2]1[CH:18]=[CH:6][C:5]2[O:10][CH2:9][CH2:8][CH:20]([C:19]([OH:22])=[O:21])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13014146HCID 13014146, compound

Product 2

HCID 313Hydrochloric AcidHCID 139537956-Chloro-3,4-dihydro-2H-1-benzopyran-4-carboxylic acid

Procedure

Following the procedure of Example 2, 6-chloro-4-cyano-4-trimethylsilyloxy-3,4-dihydro-2H-1-benzopyran (6.0 g.) and stannous chloride dihydrate (30 g.) were reacted in glacial acetic acid (25 ml.) and concentrated hydrochloric acid (25 ml.) to form 6-chloro-3,4-dihydro-2H-1-benzopyran-4-carboxylic acid. Filtration and chromatography over silica gel (300 ml.) eluted with chloroform:hexane (1:1) yielded 2.91 g. of product, m.p. 90°-90.5° C. (sublimed).

Sources & evidence

ORD record
ord-4dbbb2b0112f4633b003ddc06b5550aa
Source dataset
uspto-grants-1980_07
Patent number
US04210663

Reaction notes

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