Hydrogen Bromide → HCID 21329824, compound

HRID 614000Notes

Reaction equation

HRID 614000 reaction equation
[CH2:1]([C:4]1[C:12]([O:13]C)=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[OH:15])[CH:2]=[CH2:3].Br>C(O)(=O)C>[OH:13][C:12]1[C:4]2[CH2:1][CH:2]([CH3:3])[O:15][C:5]=2[CH:6]=[C:7]([C:8]([OH:10])=[O:9])[CH:11]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 21329830HCID 21329830, compound

Product 1

HCID 21329824HCID 21329824, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 30 grams of 4-allyl-3-hydroxy-5-methoxybenzoic acid, 150 cc of glacial acetic acid and 45 cc of 48%HBr is heated to the reflux temperature for 8 hours. After this time the reaction mixture is concentrated to dryness and the obtained residue, ground with water and filtered is crystallized from ethyl ether-petroleum ether. The product is obtained in a yield of 19.9 grams (71 percent of theoretical) and has a melting point of 181°-184° C.

Workup

  1. temperatureis heated to the reflux temperature for 8 hours
  2. concentrationAfter this time the reaction mixture is concentrated to dryness
  3. filtrationthe obtained residue, ground with water and filtered
  4. customis crystallized from ethyl ether-petroleum ether
  5. customThe product is obtained in a yield of 19.9 grams (71 percent of theoretical)

Sources & evidence

ORD record
ord-f33bba70eec64a3abf43aed49061e5dd
Source dataset
uspto-grants-1979_03
Patent number
US04143055

Reaction notes

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