Sodium Hydroxide → 2-Diphenylphosphinylmethyl-2'-methyl-1,1'-binaphthyl

HRID 2397Notes

Reaction equation

HRID 2397 reaction equation
[Br-].[C:2]1([P+:8]2([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:14][C:13]3[CH:15]=[CH:16][C:17]4[C:22]([C:12]=3[C:11]3[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=5[CH:29]=[CH:30][C:10]=3[CH2:9]2)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:37].[Na+]>C(O)C>[C:2]1([P:8]([CH2:9][C:10]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:11]=2[C:12]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:13]=2[CH3:14])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:37])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 110060894,4-diphenyl-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]phosphepinium bromide

Product 1

HCID 157892202-Diphenylphosphinylmethyl-2'-methyl-1,1'-binaphthyl

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 g (7.3 mmol) of 4,4-diphenyl-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]phosphepinium bromide are suspended in a mixture of 80 ml of 2N sodium hydroxide solution and 30 ml of ethanol and heated to boiling for 4 hours. The reaction solution is subsequently evaporated to dryness at 12 torr/40° C. The residue is taken up in 80 ml of dichloromethane and extracted twice with 30 ml of water each time. The organic phase is dried over sodium sulfate and evaporated to dryness at 12 torr/40° C. This gives colorless crystals (melting point: 199.5° C.).

Workup

  1. temperatureheated
  2. customThe reaction solution is subsequently evaporated to dryness at 12 torr/40° C
  3. extractionextracted twice with 30 ml of water each time
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated to dryness at 12 torr/40° C

Sources & evidence

ORD record
ord-86e31c9534414a65b91ab486505f6497
Source dataset
uspto-grants-1998_03
Patent number
US05728886

Reaction notes

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