Ammonia → 2-Hydroxymethyl-2-n-propylpropan-1,3-dithiol

HRID 1494671Notes

Reaction equation

HRID 1494671 reaction equation
C([S:8][CH2:9][C:10]([CH2:16][S:17]CC1C=CC=CC=1)([CH2:13][CH2:14][CH3:15])[CH2:11][OH:12])C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>C(OCC)C.CO>[OH:12][CH2:11][C:10]([CH2:13][CH2:14][CH3:15])([CH2:16][SH:17])[CH2:9][SH:8]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 193733282,2-Di(benzylthiomethyl)pentan-1-ol

Product 1

HCID 193733022-Hydroxymethyl-2-n-propylpropan-1,3-dithiol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2,2-Di(benzylthiomethyl)pentan-1-ol (8.0 g.) in dry diethyl ether (150 ml) was added to liquid ammonia (500 ml) which was stirred under nitrogen at -70° . Sodium (8.0 g.) was added in small pieces and the mixture was stirred at -70° for 3 hours. The mixture was allowed to warm to 20° and solid ammonium chloride (20 g.) was added. This was followed by careful addition of methanol (100 ml) to destroy excess sodium. Water (200 ml) was added and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. 2-Hydroxymethyl-2-n-propylpropan-1,3-dithiol was obtained as a colourless oil (4.6 g.).

Workup

  1. stirringthe mixture was stirred at -70° for 3 hours
  2. temperatureto warm to 20°
  3. customto destroy excess sodium
  4. additionWater (200 ml) was added
  5. extractionthe aqueous mixture was extracted with diethyl ether
  6. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f8f756fc9f334db4a2ec9b7d443f1695
Source dataset
uspto-grants-1991_06
Patent number
US05026874

Reaction notes

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