Hydrochloric Acid → HCID 21470013, compound

HRID 1938812Notes

Reaction equation

HRID 1938812 reaction equation
[ClH:1].[OH:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5]O.[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>C(#N)C>[Cl-:1].[OH:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5][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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 4802532-(hydroxymethyl)-4-methoxyphenol

Product 1

HCID 21470013HCID 21470013, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In the course of 30 minutes, at from 40° to 60°, 18 g of hydrogen chloride are introduced into a solution of 49.8 g of 2-hydroxy-5-methoxy-benzyl alcohol and 115.8 g of triphenylphosphane in 150 ml of acetonitrile. The reaction mixture is then stirred for 5 hours at 75°, the product beginning to crystallise after approx. 30 minutes. The reaction mixture is cooled to 0°, stirred for a further one hour and then at that temperature the crystals are filtered off with suction. [(2-Hydroxy-5-methoxy-phenyl)methyl]-triphenyl-phosphonium chloride is thus obtained in the form of colourless crystals [m.p.: 270° (decomposition); IR (KBr): 2990, 1585, 1395, 1295, 1240, 1145, 995 cm-1 ; 1H-NMR (360 MHz, CH3OH-d4 : 3.47 (s, 3H, OCH3), 4.74 (d, 2H, CH2P+), 6.40 (dd, 1H), 6.62 (d, 1H), 6.73 (m, 1H), 7.56 to 7.72 (m, 12H), 7.87 (m, 3H) ppm]; yield 78% of the theoretical yield.

Workup

  1. customto crystallise after approx. 30 minutes
  2. temperatureThe reaction mixture is cooled to 0°
  3. stirringstirred for a further one hour
  4. filtrationat that temperature the crystals are filtered off with suction

Sources & evidence

ORD record
ord-4254baae3aec43eaac646c6e37b9e9cd
Source dataset
uspto-grants-1997_12
Patent number
US05693807

Reaction notes

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