Ammonia → 3,3-Dimethyl-2-mercaptomethylbutan-1-ol

HRID 346254Notes

Reaction equation

HRID 346254 reaction equation
N.C([O:9][CH2:10][CH:11]([CH2:16][S:17]CC1C=CC=CC=1)[C:12]([CH3:15])([CH3:14])[CH3:13])C1C=CC=CC=1.[Na].[Cl-].[NH4+]>C(OCC)C.O.CO>[CH3:13][C:12]([CH3:15])([CH3:14])[CH:11]([CH2:16][SH:17])[CH2:10][OH:9]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 199906322-Benzylthiomethyl-3,3-dimethylbutyl benzyl ether

Product 1

HCID 199906203,3-Dimethyl-2-mercaptomethylbutan-1-ol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

Anhydrous liquid ammonia (400 ml) was stirred at -70°, under a current of nitrogen. 2-Benzylthiomethyl-3,3-dimethylbutyl benzyl ether (7.0 g) in dry diethyl ether (100 ml) was added and this was followed by sodium (4.0 g) in small pieces. The resulting mixture was stirred at -70° for 3 hours and then allowed to warm up to 20° C. Ammonium chloride (20 g) was added followed by dry methanol (70 ml). When all the sodium had dissolved, water was added and the mixture was extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. 3,3-Dimethyl-2-mercaptomethyl-butan-1-ol was obtained as a pale yellow oil (2.8 without further purification.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe ethereal extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3984c6e8ab1c4285a9da9710a512b12a
Source dataset
uspto-grants-1991_10
Patent number
US05061726

Reaction notes

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