Water → Benzyl Chloride

HRID 1287418Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10](CC2C=CC=CC=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[ClH:25].N1C=CC=CC=1.[OH2:32]>C(Cl)(Cl)Cl>[C:12]1([C:11](=[O:32])[CH2:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:32])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[Cl:25][CH2:9][C:6]1[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 210 °C

Procedure

To 4.3 g (0.0136 mole) of 1-(4-methoxyphenyl)-2-benzyl-3-phenylpropane was added 4 g (0.0346 mole) of pyridine hydrochloride and heated to 210°C for 5 hours. The mixture was cooled, and 300 ml H2O and 300 ml chloroform were added. Chloroform layer was separated, washed with 4 × 250 ml H2O and dried over anhydrous MgSO4. Chloroform was removed at reduced pressure. The residue was distilled at 210°-215°C/0.3 mm. Yield 3.5 g (85.16%). This material can also be obtained by alkylation of 1-phenyl-3-(4-methoxyphenyl)-1-propanone or 1-(4-methoxyphenyl)-3-phenyl-1-propanone with α-chlorotoluene as carried out in Example I, followed by demethylation with pyridine hydrochloride and reduction of the carbonyl function.

Workup

temperatureThe mixture was cooled
customChloroform layer was separated
washwashed with 4 × 250 ml H2O
dry with materialdried over anhydrous MgSO4
customChloroform was removed at reduced pressure
distillationThe residue was distilled at 210°-215°C/0.3 mm

Sources & evidence

ORD record: ord-f2e344ab649f4b388033da756012b183
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03984501

Reaction notes

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