Hydrogen Bromide → 6-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 1955461

Reaction equation

HRID 1955461 reaction equation
C([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C:22]([OH:24])=[O:23])[CH:16]=[CH:15]2)CCCCCCCCC.Br>C(O)(=O)C>[OH:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH2:18][CH:17]([C:22]([OH:24])=[O:23])[CH2:16][CH2:15]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 103591672-Naphthalenecarboxylic acid, 6-(decyloxy)-

Product 1

HCID 190700016-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

16.6 g (50 mmol) of the 6-decyloxynaphthalene-2-carboxylic acid obtained in the first stage was heated under reflux at 130° C. for 7 hours in the presence of 250 cc of acetic acid and 86.5 g (0.5 mol) of 47% hydrobromic acid. To the reaction mixture was added distilled water, and then the resulting mixture was concentrated under reduced pressure to obtain 10.60 g (50 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid.

Workup

  1. temperaturewas heated
  2. additionTo the reaction mixture was added
  3. distillationdistilled water
  4. concentrationthe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bce8560a0c644c2bb4ff2578e5abcfbc
Source dataset
uspto-grants-1998_07
Patent number
US05776365

Linked notes

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