Diethyl Ether → 4-Methoxybenzaldehyde

HRID 1657515Notes

Reaction equation

HRID 1657515 reaction equation
P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CCCC)CCCC)CCC.Br[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1.[C]=O.[H][H].C[CH2:47][O:48]CC>>[CH3:41][O:40][C:37]1[CH:38]=[CH:39][C:34]([CH:47]=[O:48])=[CH:35][CH:36]=1

Participants

7

Reactant 6

HCID 3283Diethyl EtherHCID 7622TributylamineHCID 77304-BromoanisoleHCID 11776TriphenylphosphineHCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 312444-Methoxybenzaldehyde

Conditions

Temperature
150 °C

Procedure

A mixture of 0.25 mmole PdBr2 [P(C6H5)3 ]2, 19 mmoles tri-n-butylamine and 17.2 mmoles p-bromoanisole was placed in a 45 ml pressure vessel and pressured to 1450 psig with a 1:2 mixture of carbon monoxide and hydrogen. The reaction mixture was heated to 150°C for 10 hrs. with magnetic stirring during which time the gas pressure dropped to 1100 psig. After cooling and venting the reaction mixture was diluted with ether, washed with dilute aqueous hydrochloric acid, dried over anhydrous magnesium sulfate and distilled under reduced pressure. There was obtained 1.97 g of p-methoxybenzaldehyde, b.p. 73°-75°C at 0.7 mm which is 84% of the theoretical amount.

Workup

  1. customwas placed in a 45 ml pressure vessel
  2. additiondropped to 1100 psig
  3. temperatureAfter cooling
  4. washwashed with dilute aqueous hydrochloric acid
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-8e6d57346bc84f18beba69036d5f4b6a
Source dataset
uspto-grants-1976_06
Patent number
US03960932

Reaction notes

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