Acetic Acid → 6-Chloro-7-hydroxychroman-4-carboxylic acid

HRID 1626487Notes

Reaction equation

HRID 1626487 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6]C2(O[Si](C)(C)C)C#N.[C:20]([OH:23])(=[O:22])[CH3:21]>Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][CH:21]2[C:20]([OH:23])=[O:22]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67287343HCID 67287343, compound

Product 1

HCID 670804286-Chloro-7-hydroxychroman-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-chloro-7-hydroxy-4-(trimethylsilyloxy)chroman-4-carbonitrile (129 g, 433 mmol) and SnCl2 dihydrate (293 g, 1299 mmol) in concentrated HCl (435 ml) and glacial acetic acid (435 ml) was heated to 125° C. and stirred for 12 hours. The reaction was taken up in ethyl acetate (500 ml) and washed with water (3×500 ml), dried over magnesium sulfate, filtered and concentrated to give the desired compound (99 g, 100%).

Workup

  1. washwashed with water (3×500 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a3f43f1b99ab46c2849b0c39bb358ce2
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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