Sodium Hydroxide → tert-Butyl (triphenylphosphoranylidene) acetate

HRID 1722233Notes

Reaction equation

HRID 1722233 reaction equation
[Br-].[C:2]([CH2:9][P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].[OH-].[Na+]>O>[C:2]([CH:9]=[P:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2733853(tert-Butoxycarbonylmethyl)triphenylphosphonium Bromide

Product 1

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of the carbo-t-butoxymethyl triphenylphosphonium bromide (55.8 g, 122 mmol) in water (400 ml) was treated with sodium hydroxide (4.7 g, 117 mml) in water (100 ml). The mixture was stirred for 16 hours and the solid collected to give 43.7 g (95% of theory) of carbo-t-butoxymethylene triphenylphosphorane.

Workup

  1. customthe solid collected

Sources & evidence

ORD record
ord-ea072243946242229bc2a372745f0ad7
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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