4-Hydroxybenzoic Acid → HCID 54078988, compound

HRID 1088192Notes

Reaction equation

HRID 1088192 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][C@@H:12]([CH:16]([CH3:18])[CH3:17])[C:13](Cl)=[O:14].Cl>N1C=CC=CC=1>[Cl:11][C@@H:12]([CH:16]([CH3:18])[CH3:17])[C:13]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:14]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 12239728HCID 12239728, compound

Product 1

HCID 54078988HCID 54078988, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Hydroxybenzoic acid (8.9 g, 0.065 moles) is dissolved in 20 mL of absolute pyridine and 10 g (0.065 moles) of (S)-(+)-2-chloro-3-methylbutyryl chloride are added dropwise with stirring at 0° to 5° C. The mixture is allowed to stand for 4 hours at room temperature and then poured onto ice/conc. HCl (200 g/30 mL). The precipitate is filtered off with suction and washed several times with dilute HCl and water. The residue is recrystallized from methanol/water.

Workup

  1. additionpoured onto ice/conc
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed several times with dilute HCl and water
  4. customThe residue is recrystallized from methanol/water

Sources & evidence

ORD record
ord-89d77528297d4a9b9aad27c0b4be1b72
Source dataset
uspto-grants-1990_10
Patent number
US04961876

Reaction notes

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