tert-Butyl methyl ether → HCID 131723218, compound

HRID 1935297Notes

Reaction equation

HRID 1935297 reaction equation
[C:1]([C@@H:7]([C@H:9]([C:11]([O:13]C(C)C)=[O:12])[OH:10])[OH:8])([O:3]C(C)C)=[O:2].C[O:18][CH:19](OC)[CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26].C([O-])(O)=O.[Na+].[CH3:36][C:37](OC)(C)[CH3:38]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH:20]([C:7]([C:1]([OH:3])=[O:2])([OH:8])[C:9]([CH:37]([CH3:38])[CH3:36])([OH:10])[C:11]([OH:13])=[O:12])([CH3:21])[CH3:19].[CH3:27][C:25](=[CH:24][CH2:23][CH2:22][C:21](=[CH:20][CH:19]=[O:18])[CH3:28])[CH3:26]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 241913,7-Dimethyl-2,6-octadienal dimethyl acetalHCID 516892Sodium BicarbonateHCID 6453580Diisopropyl tartrate

Product 1

HCID 131723218HCID 131723218, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)Catalyst

Conditions

Temperature
55 °C

Procedure

A solution of 20.0 g (85.5 mmol) (R,R)-diisopropyl tartrate, 33.85 g (170.9 mmol) citral dimethyl acetal and 0.5 g pyridinium p-toluene sulfonate in 350 ml MTBE is heated at reflux temperature (55° C.) for 5 h. The clear yellow; reaction mixture is allowed to cool to room temperature and 150 ml saturated NaHCO3 solution is added. The aqueous layer is separated and washed twice with 150 ml MTBE. The combined organic layers are washed with 100 ml brine, dried (MgSO4) and concentrated in vacuo (rotary evaporator). Using a Büchi-Kugelrohrofen the oily residue (47.1 g) is dried in high vacuum (0.1 torr) at 110° C. to give 25.5 g (81%) citral diisopropyl tartrate 1. 1H-NMR: 1.30 (d, CH3), 1.31 (d, CH3), 1.61 (s, CH3), 1.68 (s, CH3), 1.79 (d, CH3), 2.0-2.2 (m, 4H, CH2), 4.61 (m, 1H), 4.67 (m, 1H), 5.0-5.2 (m, 3H), 5.36 (m, 1H), 5.91 (dd, 1H); MS: 368 (3, M+), 281 (5), 245 (8), 69 (100), 41 (83).

Workup

  1. customreaction mixture
  2. temperatureto cool to room temperature
  3. customThe aqueous layer is separated
  4. washwashed twice with 150 ml MTBE
  5. washThe combined organic layers are washed with 100 ml brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo (rotary evaporator)
  8. customis dried in high vacuum (0.1 torr) at 110° C.

Sources & evidence

ORD record
ord-f87bc41904b24e3fbd08a873cde9da44
Source dataset
uspto-grants-2002_05
Patent number
US06387431B1

Reaction notes

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