Hydrochloric Acid → 4-Hydroxy-1-indanone

HRID 514793

Reaction equation

HRID 514793 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+].[O:7]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][C:8]1=[O:9].Cl>O>[OH:7][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:12]=1[CH2:11][CH2:10][C:8]2=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 660DihydrocoumarinHCID 5234Sodium ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5905474-Hydroxy-1-indanoneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Anhydrous aluminum chloride (550 g, 4.135 mol, 4 eq) and sodium chloride (105 g, 1.795 mol, 2.7 eq) were mixed and heated to 150° C. Dihydrocoumarin (75) (100 g, 675.7 mol, 1 eq) was added slowly maintaining the internal temperature between 150-160° C. After the addition, the temperature was increased to 200° C. and the reaction mixture stirred for 1.5 h, and while hot, poured into a porcelain dish to cool. The solidified mass was broken and added to a vigorously stirred mixture of ice and water (4 L) containing 400 mL conc. HCl. The resulting suspension was stirred for 1 h, filtered, washed with water and dried to give 85 g (85%) of crude 4-hydroxy-1-indanone (76) as a grey solid. It was sufficiently pure to be used in the next step.

Workup

  1. temperaturemaintaining the internal temperature between 150-160° C
  2. additionAfter the addition
  3. temperaturethe temperature was increased to 200° C.
  4. additionwhile hot, poured into a porcelain dish
  5. temperatureto cool
  6. stirringThe resulting suspension was stirred for 1 h
  7. filtrationfiltered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-db187242ee174b2d94926bf230aaddf1
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Linked notes

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