Ammonium → 3-Hexadecanol, 3,7,11,15-tetramethyl-

HRID 621751Notes

Reaction equation

HRID 621751 reaction equation
[CH3:1][C@H:2]([CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:3][CH2:4]Br.[Mg].CO[C:20]1[C:25](C)=C(C)C(OC)=[C:22](C)[C:21]=1[CH2:31]C[C@]1(C)OC1.[NH4+].C(OCC)(=[O:40])C>C(OCC)C>[CH3:1][C:2]([OH:40])([CH2:6][CH2:7][CH2:8][CH:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH2:14][CH2:25][CH2:20][CH:21]([CH3:31])[CH3:22])[CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 223AmmoniumHCID 8857Ethyl AcetateHCID 5462224MagnesiumHCID 13191851(3R,7R)-1-bromo-3,7,11-trimethyldodecaneHCID 18602184(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxy-butane

Product 1

HCID 30209773-Hexadecanol, 3,7,11,15-tetramethyl-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5.8 mmol of (3R,7R)-3,7,11-trimethyldodecyl bromide are heated at reflux for 1/4 hour in 20 ml of ethyl acetate with activated magnesium. Then, there are added at 0° C. 1 g of (S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-epoxybutane and 0.9 g of copper(I)-2-propylacetylide (or 1.2 g of copper(I) bromide/dimethyl sulphide complex). The temperature of the reaction mixture is subsequently left to rise to room temperature and the mixture is stirred overnight. 10 ml of ammonium with ethyl ether. The extract is dried and concentrated, and the residue is distilled in a bulb-tube (b.p.0.01 =140° C.). There are obtained 1.28 g (72%) (or 1.41 g (79%) of (3R,7R,11R)-1-)2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethylhexadecan-3-ol as a colourless oil.

Workup

  1. additionThen, there are added at 0° C
  2. waitThe temperature of the reaction mixture is subsequently left
  3. customto rise to room temperature
  4. customThe extract is dried
  5. concentrationconcentrated
  6. distillationthe residue is distilled in a bulb-tube (b.p.0.01 =140° C.)

Sources & evidence

ORD record
ord-45ee9a40b9c84dffb8d5f6c96f22eb63
Source dataset
uspto-grants-1989_04
Patent number
US04824972

Reaction notes

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