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Ammonia → 2-(2,2-Dimethylpropyl)-2-hydroxymethylpropane-1,3-diol

HRID 1089147
Notes
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Reaction equation

HRID 1089147 reaction equation
C([O:8][CH2:9][C:10]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH2:13][OH:14])[CH2:11][OH:12])C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>C(OCC)C>[CH3:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:10]([CH2:9][OH:8])([CH2:13][OH:14])[CH2:11][OH:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 150219552-Benzyloxymethyl-2-(2,2-dimethylpropyl)-propan-1,3-diol

Product 1

HCID 189533432-(2,2-Dimethylpropyl)-2-hydroxymethylpropane-1,3-diol

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Procedure

2-Benzyloxymethyl-2-(2,2-dimethylpropyl)-propan-1,3-diol (5.5 g.) in dry diethyl ether (50 ml.) was added to liquid ammonia (200 ml.) at -70°. Sodium (2.5 g.) was added to the stirred solution. Stirring was maintained at -70°, for 1 hour. The mixture was allowed to warm up to -30° and solid ammonium chloride (15 g.) was added cautiously. The ammonia was removed from the reaction mixture under a current of nitrogen. Methanol (25 ml.) was added to the stirred mixture to destroy residual sodium. Dichloromethane (400 ml.) was added and the mixture was filtered. The filtrates were evaporated in vacuo. 2-(2,2-Dimethylpropyl)-2-hydroxymethyl-propan-1,3-diol was obtained as a colourless solid (3.5 g.).

Workup

  1. temperaturewas maintained at -70°, for 1 hour
  2. temperatureto warm up to -30°
  3. customThe ammonia was removed from the reaction mixture under a current of nitrogen
  4. additionMethanol (25 ml.) was added to the stirred mixture
  5. customto destroy residual sodium
  6. additionDichloromethane (400 ml.) was added
  7. filtrationthe mixture was filtered
  8. customThe filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-40f681ab6d5344ee8af561117208c064
Source dataset
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04965257

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes