Hydrochloric Acid → 4-[3-(3-Acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acid

HRID 986701Notes

Reaction equation

HRID 986701 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH2:35][CH2:36][CH3:37])=[C:7]([CH:29]=[CH:30][C:31]=1[C:32](=[O:34])[CH3:33])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([C:17]([O:19]C2CCCCO2)=[O:18])=[CH:15][C:14]=1[Br:28])(=[O:3])[CH3:2].Cl.C(Cl)(Cl)Cl>O1CCCC1>[C:1]([O:4][C:5]1[C:6]([CH2:35][CH2:36][CH3:37])=[C:7]([CH:29]=[CH:30][C:31]=1[C:32](=[O:34])[CH3:33])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[Br:28])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 20157038HCID 20157038, compound

Product 1

HCID 137456304-[3-(3-Acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acidYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (10 ml) was dissolved tetrahydropyranyl 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoate (1.3 g). To the solution was added 1N HCl (1 ml), which was left standing at room temperature for one hour, followed by addition of chloroform (60 ml). The mixture was washed with water sufficiently and dried with sodium sulfate. Then, the solvent was evaporated off. The residue was crystallized with isopropyl ether, followed by recrystallization from aqueous alcohol to give 0.7 g of 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acid as crystals, m.p. 155°-156° C.

Workup

  1. waitwas left
  2. washThe mixture was washed with water sufficiently
  3. dry with materialdried with sodium sulfate
  4. customThen, the solvent was evaporated off
  5. customThe residue was crystallized with isopropyl ether
  6. customfollowed by recrystallization from aqueous alcohol

Sources & evidence

ORD record
ord-f01842d832ca43f384e87ba37be2f522
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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