4-Hydroxybenzoic Acid → HCID 54031748, compound

HRID 2397021Notes

Reaction equation

HRID 2397021 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[CH3:15][C@@H:16]([CH2:19][CH3:20])[CH2:17]O.S(=O)(=O)(O)O.OC1C=CC(C(O)=O)=CC=1>C(Cl)(Cl)Cl.C1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH2:15][C@@H:16]([CH3:17])[CH2:19][CH3:20])=[O:13])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 855576-Hydroxy-2-naphthoic acidHCID 2723602(S)-2-methyl-1-butanol

Product 1

HCID 54031748HCID 54031748, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

In a flask equipped with a Dean-Stark trap 6.78 g (0.036 mole) 6-hydroxyl-2-naphthaleneformic acid, 4.76 g (0.054 mole) (S)-2-methyl-1-butanol, 0.2 ml sulfuric acid and 15 ml anhydrous benzene were charged and refluxed for about 15 hours until all the 4-hydroxybenzoic acid was dissolved. The esterification reaction mixture was cooled to room temperature, extracted with ethyl ether, and washed with 5% (w/w) sodium hydrogen carbonate aqueous solution. The ethyl ether layer was collected, concentrated, and purified with column chromatography (ethyl acetate/n-hexane) to obtained light yellow solid. Yield: 93%. The optical rotation: [α]25D =+2.97 (c=1.0 g/dl, chloroform).

Workup

  1. additionwere charged
  2. dissolutionwas dissolved
  3. customThe esterification reaction mixture
  4. extractionextracted with ethyl ether
  5. washwashed with 5% (w/w) sodium hydrogen carbonate aqueous solution
  6. customThe ethyl ether layer was collected
  7. concentrationconcentrated
  8. custompurified with column chromatography (ethyl acetate/n-hexane)
  9. customto obtained light yellow solid

Sources & evidence

ORD record
ord-7179dae1b4034937a903060cd4716032
Source dataset
uspto-grants-1996_02
Patent number
US05495037

Reaction notes

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