Triphenylphosphine → (3-Benzyloxypropyl)triphenylphosphonium bromide

HRID 1833759Notes

Reaction equation

HRID 1833759 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][Br:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1.C(OCC)(=O)C>[Br-:12].[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 2776064Benzyl 3-Bromopropyl Ether

Product 1

HCID 10929077(3-Benzyloxypropyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-benzyloxy-1-bromopropane (41.0 g., 0.18 mole) and triphenylphosphine (52.4 g., 0.2 mole) in benzene (500 ml.) is stirred and heated at reflux for 92 hours. After removing the solvent in vacuo, the residual gum is dissolved in acetonitrile (50 ml.) providing a pale yellow solution which is diluted with ethyl acetate (400 ml.) to incipient cloudiness and stirred at 25° for 48 hours. Deposited crystals are collected; the yield is 48 g. (53%). Recrystallization from ethyl acetate-acetonitrile (4:1) provides colorless needles, m.p. 151°-152°; pmr (CDCl3)δ2.0 (2H,m), 3.78 (4H,m), 4.49 (2H,s), 7.29 (5H,s) and 7.70 (15H,m).

Workup

  1. temperatureheated
  2. temperatureat reflux for 92 hours
  3. customAfter removing the solvent in vacuo
  4. dissolutionthe residual gum is dissolved in acetonitrile (50 ml.)
  5. customproviding a pale yellow solution which
  6. customDeposited crystals are collected
  7. customRecrystallization from ethyl acetate-acetonitrile (4:1)
  8. customprovides colorless needles, m.p. 151°-152°

Sources & evidence

ORD record
ord-339dbb39e88d45e092a98a4bce278778
Source dataset
uspto-grants-1978_01
Patent number
US04066692

Reaction notes

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