Hydrochloric Acid → Indane

HRID 2301697Notes

Reaction equation

HRID 2301697 reaction equation
OC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.Cl.[CH2:14]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1S(O)(=O)=O)[CH2:15][CH2:16]CCCCCCCCC.C(C1C=C2C(=CC=1)CCC2)=O.[OH-].[K+]>O>[CH2:16]1[C:27]2[C:26](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][CH2:15]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5780SorbitolHCID 14797Potassium HydroxideHCID 25457Dodecylbenzenesulphonic acidHCID 1216245-Indanecarboxaldehyde

Product 1

HCID 10326Indane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 400 mL reaction vessel fitted with a mechanical stirrer was charged with sorbitol (32 g, 0.18 mol), water (20 g), concentrated HCl (45 g) and dodecylbenzenesulfonic acid (0.4 g). After stirring for 10 min, 5-formylindan (29 g, 0.20 mol) was added. The mixture was stirred for 18 h, then neutralized with aqueous KOH. The solids were collected by filtration and washed with water and methanol to give Indan DBS as a white solid (14 g, 33% yield).

Workup

  1. customA 400 mL reaction vessel
  2. customfitted with a mechanical stirrer
  3. stirringThe mixture was stirred for 18 h
  4. filtrationThe solids were collected by filtration
  5. washwashed with water and methanol

Sources & evidence

ORD record
ord-c6824736c63c435084408bfbf1e7c471
Source dataset
uspto-grants-2002_12
Patent number
US06500964B2

Reaction notes

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