Iodine → 1-Benzyloxy-3-iodopropane

HRID 1758167Notes

Reaction equation

HRID 1758167 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.N1C=CC=CC=1.[CH2:28]([O:35][CH2:36][CH2:37][CH2:38]O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.C1C=CC=CC=1>[CH2:28]([O:35][CH2:36][CH2:37][CH2:38][I:20])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1049PyridineHCID 11776TriphenylphosphineHCID 3479713-Benzyloxy-1-propanol

Product 1

HCID 104686631-Benzyloxy-3-iodopropaneYield 53%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 887MethanolSolvent

Procedure

To a solution of 83.3 g. (0.318 mole) triphenylphosphine in 200 ml. benzene was added, in four portions, 80 g. (0.318 mole) of iodine. The resultant mixture was stirred 3 hours and then 50 ml. (0.618 mole) of pyridine was added followed by the slow addition of 32 g. (0.192 mole) of 3-benzyloxypropanol in 250 ml. of benzene. The reaction was stirred 15 hours longer and then diluted with 40 ml. of methanol. The mixture was filtered through diatomaceous earth and the filtrate evaporated to an oil. Distillation of the crude oil yielded 28 g. (53%) of the title compound as an oil.

Workup

  1. additionfollowed by the slow addition of 32 g
  2. additiondiluted with 40 ml
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. customthe filtrate evaporated to an oil
  5. distillationDistillation of the crude oil
  6. customyielded 28 g

Sources & evidence

ORD record
ord-00ae948dc5c7426fadb8151c24bc7583
Source dataset
uspto-grants-1983_02
Patent number
US04371720

Reaction notes

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