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

HRID 1626406Notes

Reaction equation

HRID 1626406 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, dried over magnesium sulfate, filtered and concentrated to provide the desired product (99 g, 100%).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7b6ed07088bd43289aae3d545707779b
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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