Water → HCID 70533310, compound

HRID 435449Notes

Reaction equation

HRID 435449 reaction equation
[C:1]1([C:7]2[C:8]3[O:13][CH2:12][O:11][CH:10](O)[C:9]=3[CH:15]=[CH:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:26].C(Cl)Cl.O>CCOCC.N1C=CC=CC=1>[C:1]1([C:7]2[C:8]3[O:13][CH2:12][O:11][CH:10]([Cl:26])[C:9]=3[CH:15]=[CH:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 70532672HCID 70532672, compound

Product 1

HCID 70533310HCID 70533310, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 11.6 g. (38 mmol) of 3,4-diphenylmethylenedioxybenzyl alcohol in ether (80 ml.) and pyridine (0.6 ml.) at 20° C. was added dropwise a solution of SOCl2 in ether (40 ml.). The mixture was cooled to 0°-5° C., and CH2Cl2 and water were added. The layers were separated, and the organic layer was washed with water and saturated aqueous NaCl, dried over MgSO4 and concentrated to dryness to yield 3,4-diphenylmethylenedioxybenzyl chloride (11.43 g.) as a colorless viscous oil: tlc (silica gel CH2Cl2 : Rf 0.8; ir (CCl4) no --OH--, nmr (CCl4) δ 4.34 (s, 2H), 6.74 (d,j=8) 2H, 6.67 (s, 1H), 7.1-7.6 (m, 10H). ##STR11##

Workup

  1. temperatureThe mixture was cooled to 0°-5° C.
  2. customThe layers were separated
  3. washthe organic layer was washed with water and saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-184d5f6240034e1bb527e37469b92536
Source dataset
uspto-grants-1983_08
Patent number
US04401676

Reaction notes

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