Thionyl Chloride → HCID 21278117, compound

HRID 2291851Notes

Reaction equation

HRID 2291851 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(O)[CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][CH2:9][C:10]([CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:11][CH2:12][Cl:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 21278116HCID 21278116, compound

Product 1

HCID 21278117HCID 21278117, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Crude 1-benzyloxy-2-benzyloxymethylbut-3-en-2-ol (1.42 g, 3.16 mmol) in 10 ml of CH2Cl2 was added to 0.71 g thionyl chloride (6 mmol) and 2 drops of DMF in 10 ml of CH2Cl2, and the solution was stirred for 0.5 h and evaporated in vacuum. Toluene was added and the mixture was evaporated in vacuum to yield crude 1-benzyloxy-2-benzyloxymethyl-4-chlorobut-2-ene.

Workup

  1. customevaporated in vacuum
  2. additionToluene was added
  3. customthe mixture was evaporated in vacuum

Sources & evidence

ORD record
ord-f959b40a783142a8b79da9eebd7e1735
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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