4-Hydroxybenzoic Acid → HCID 67570688, compound

HRID 342816Notes

Reaction equation

HRID 342816 reaction equation
[CH2:1]([C:5]([CH3:7])=[O:6])[CH:2]([CH3:4])C.O[C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1.[CH2:18](N(CC)CC)C.Cl[CH2:26][C:27]1C=CC(C=C)=C[CH:28]=1>O>[OH:6][C:5]1[CH:1]=[CH:2][C:4]([CH:26]=[CH:27][CH2:28][O:15][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][CH:9]=[CH:10][CH:11]=2)=[CH:18][CH:7]=1

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 7909Methyl Isobutyl KetoneHCID 8471TriethylamineHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 67570688HCID 67570688, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1500 g of methyl isobutyl ketone, 69 g of 4-hydroxybenzoic acid and 58.0 g of triethylamine were charged into a separable flask as used in Reference Example 4, and after the flask was heated to 80° C. while replacing the flask inside atmosphere with a nitrogen gas, 72.4 g of p-chloromethylstyrene was dropwise added thereto over 2 hours. Then, stirring was continued for 6 hours. After the reaction, 3 liters water was added to the reaction mixture, and powdery precipitate was recovered therefrom and washed with n-hexane, whereby 36.2 g of p-hydroxybenzoyloxymethylstyrene of the following chemical formula was obtained (yield: 30%): ##STR8##

Workup

  1. additionwas dropwise added
  2. waitwas continued for 6 hours
  3. additionwas added to the reaction mixture, and powdery precipitate
  4. customwas recovered
  5. washwashed with n-hexane, whereby 36.2 g of p-hydroxybenzoyloxymethylstyrene of the following chemical formula
  6. customwas obtained (yield: 30%)

Sources & evidence

ORD record
ord-6bca9189bb50418fac7d4ff484f98c32
Source dataset
uspto-grants-1999_01
Patent number
US05859144

Reaction notes

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