Hydrochloric Acid → 5-(Chloromethyl)-2,3-dihydro-1h-indene

HRID 330292Notes

Reaction equation

HRID 330292 reaction equation
[CH2:1]1[C:9]2[C:4](=C[CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C=O.[ClH:12].OP(O)(O)=O.CCO[CH2:21][CH3:22]>C(O)(=O)C>[Cl:12][CH2:6][C:7]1[CH:8]=[C:9]2[C:4](=[CH:21][CH:22]=1)[CH2:3][CH2:2][CH2:1]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1004Phosphoric AcidHCID 3283Diethyl EtherHCID 10326Indane

Product 1

HCID 2331495-(Chloromethyl)-2,3-dihydro-1h-indene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of indan (50.0 g, 0.423 mol), paraformaldehyde (23.3 g), concentrated HCl (74 mL), 85% H3PO4 (33 mL), and acetic acid (54 mL) was heated at 95° C. for 6 hours. The mixture was cooled and diluted with ether (200 mL). The organic phase was separated and washed with H2O (2×200 mL), saturated aqueous NaHCO3 (200 mL), H2O (200 mL), dried (MgSO4), and concentrated. The crude product was distilled under high vacuum (0.8 mm) to give 35.2 g (50%) as a colorless oil, b.p. 89° C.

Workup

  1. temperatureThe mixture was cooled
  2. customThe organic phase was separated
  3. washwashed with H2O (2×200 mL), saturated aqueous NaHCO3 (200 mL), H2O (200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. distillationThe crude product was distilled under high vacuum (0.8 mm)
  7. customto give 35.2 g (50%) as a colorless oil, b.p. 89° C.

Sources & evidence

ORD record
ord-4a6384bc14844bca979bdb7c534fd074
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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